1: H2 / palladium black / acetic acid / 72 h / Ambient temperature 2: 74 percent / trifluoroacetic acid / D2O / 50 h / Ambient temperature View Scheme

1: 100 percent / hydrogen / palladium black / methanol / 1 h / Ambient temperature 2: aq. sodium bicarbonate / diethyl ether / 1.5 h / 0 °C 3: 75 percent / pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 1.5 h / Ambient temperature 4: 59 percent / CH2Cl2 / 16 h / Ambient temperature 5: 61 percent / hydrogen / palladium black / methanol / 48 h 6: H2 / palladium black / acetic acid / 72 h / Ambient temperature 7: 74 percent / trifluoroacetic acid / D2O / 50 h / Ambient temperature View Scheme

1: hydrogen / palladium on carbon / methanol / 6 h 2: H2 / palladium black / acetic acid / 72 h / Ambient temperature 3: 74 percent / trifluoroacetic acid / D2O / 50 h / Ambient temperature View Scheme

1: 97 percent / camphorsulphonic acid / acetone / 16 h / Ambient temperature 2: pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 2 h / Ambient temperature; molecular sieve 3 A 3: sodium borohydride / ethanol / 1 h / 0 °C 4: pyridine / CH2Cl2 / 8 h / -20 °C 5: sodium azide / dimethylformamide / 16 h / Ambient temperature 6: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature 7: 100 percent / hydrogen / palladium black / methanol / 1 h / Ambient temperature 8: aq. sodium bicarbonate / diethyl ether / 1.5 h / 0 °C 9: 75 percent / pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 1.5 h / Ambient temperature 10: 59 percent / CH2Cl2 / 16 h / Ambient temperature 11: 61 percent / hydrogen / palladium black / methanol / 48 h 12: H2 / palladium black / acetic acid / 72 h / Ambient temperature 13: 74 percent / trifluoroacetic acid / D2O / 50 h / Ambient temperature View Scheme

1: sodium borohydride / ethanol / 1 h / 0 °C 2: pyridine / CH2Cl2 / 8 h / -20 °C 3: sodium azide / dimethylformamide / 16 h / Ambient temperature 4: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature 5: 100 percent / hydrogen / palladium black / methanol / 1 h / Ambient temperature 6: aq. sodium bicarbonate / diethyl ether / 1.5 h / 0 °C 7: 75 percent / pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 1.5 h / Ambient temperature 8: 59 percent / CH2Cl2 / 16 h / Ambient temperature 9: 61 percent / hydrogen / palladium black / methanol / 48 h 10: H2 / palladium black / acetic acid / 72 h / Ambient temperature 11: 74 percent / trifluoroacetic acid / D2O / 50 h / Ambient temperature View Scheme

1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature 2: 100 percent / hydrogen / palladium black / methanol / 1 h / Ambient temperature 3: aq. sodium bicarbonate / diethyl ether / 1.5 h / 0 °C 4: 75 percent / pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 1.5 h / Ambient temperature 5: 59 percent / CH2Cl2 / 16 h / Ambient temperature 6: 61 percent / hydrogen / palladium black / methanol / 48 h 7: H2 / palladium black / acetic acid / 72 h / Ambient temperature 8: 74 percent / trifluoroacetic acid / D2O / 50 h / Ambient temperature View Scheme

1: sodium azide / dimethylformamide / 16 h / Ambient temperature 2: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature 3: 100 percent / hydrogen / palladium black / methanol / 1 h / Ambient temperature 4: aq. sodium bicarbonate / diethyl ether / 1.5 h / 0 °C 5: 75 percent / pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 1.5 h / Ambient temperature 6: 59 percent / CH2Cl2 / 16 h / Ambient temperature 7: 61 percent / hydrogen / palladium black / methanol / 48 h 8: H2 / palladium black / acetic acid / 72 h / Ambient temperature 9: 74 percent / trifluoroacetic acid / D2O / 50 h / Ambient temperature View Scheme

1: pyridine / CH2Cl2 / 8 h / -20 °C 2: sodium azide / dimethylformamide / 16 h / Ambient temperature 3: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature 4: 100 percent / hydrogen / palladium black / methanol / 1 h / Ambient temperature 5: aq. sodium bicarbonate / diethyl ether / 1.5 h / 0 °C 6: 75 percent / pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 1.5 h / Ambient temperature 7: 59 percent / CH2Cl2 / 16 h / Ambient temperature 8: 61 percent / hydrogen / palladium black / methanol / 48 h 9: H2 / palladium black / acetic acid / 72 h / Ambient temperature 10: 74 percent / trifluoroacetic acid / D2O / 50 h / Ambient temperature View Scheme

1: pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 2 h / Ambient temperature; molecular sieve 3 A 2: sodium borohydride / ethanol / 1 h / 0 °C 3: pyridine / CH2Cl2 / 8 h / -20 °C 4: sodium azide / dimethylformamide / 16 h / Ambient temperature 5: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 4 h / Ambient temperature 6: 100 percent / hydrogen / palladium black / methanol / 1 h / Ambient temperature 7: aq. sodium bicarbonate / diethyl ether / 1.5 h / 0 °C 8: 75 percent / pyridinium chlorochromate, molecular sieve 3 A / CH2Cl2 / 1.5 h / Ambient temperature 9: 59 percent / CH2Cl2 / 16 h / Ambient temperature 10: 61 percent / hydrogen / palladium black / methanol / 48 h 11: H2 / palladium black / acetic acid / 72 h / Ambient temperature 12: 74 percent / trifluoroacetic acid / D2O / 50 h / Ambient temperature View Scheme

dimethylsulfide; borane; trifluoroacetic acid Yield given. Multistep reaction;