hydrogen; palladium on activated charcoal in ethyl acetate 9 h;

1: 32 percent / pyridine, 4-(N,N-dimethylamino)pyridine / 91 h / Ambient temperature 2: 1) (COCl)2, DMSO, 2) NEt3 / 1) CH2Cl2, -78 deg C, 25 min, 2a) -78 deg C, 5 min, b) to.r.t. 3: 77 percent / LiBr, NEt3 / acetonitrile / 16 h / Ambient temperature 4: 80 percent / nBu4NF*3H2O, HOAc / tetrahydrofuran / 48 h 5: 89 percent / H2 / 10percent Pd/C / ethyl acetate / 9 h View Scheme

1: 32 percent / pyridine, 4-(N,N-dimethylamino)pyridine / 91 h / Ambient temperature 2: 1) (COCl)2, DMSO, 2) NEt3 / 1) CH2Cl2, -78 deg C, 25 min, 2a) -78 deg C, 5 min, b) to.r.t. 3: 77 percent / LiBr, NEt3 / acetonitrile / 16 h / Ambient temperature 4: 80 percent / nBu4NF*3H2O, HOAc / tetrahydrofuran / 48 h 5: 89 percent / H2 / 10percent Pd/C / ethyl acetate / 9 h View Scheme

1: 77 percent / LiBr, NEt3 / acetonitrile / 16 h / Ambient temperature 2: 80 percent / nBu4NF*3H2O, HOAc / tetrahydrofuran / 48 h 3: 89 percent / H2 / 10percent Pd/C / ethyl acetate / 9 h View Scheme

1: 1) (COCl)2, DMSO, 2) NEt3 / 1) CH2Cl2, -78 deg C, 25 min, 2a) -78 deg C, 5 min, b) to.r.t. 2: 77 percent / LiBr, NEt3 / acetonitrile / 16 h / Ambient temperature 3: 80 percent / nBu4NF*3H2O, HOAc / tetrahydrofuran / 48 h 4: 89 percent / H2 / 10percent Pd/C / ethyl acetate / 9 h View Scheme

1: 85 percent / LiAlH4 / diethyl ether / 89 h 2: 32 percent / pyridine, 4-(N,N-dimethylamino)pyridine / 91 h / Ambient temperature 3: 1) (COCl)2, DMSO, 2) NEt3 / 1) CH2Cl2, -78 deg C, 25 min, 2a) -78 deg C, 5 min, b) to.r.t. 4: 77 percent / LiBr, NEt3 / acetonitrile / 16 h / Ambient temperature 5: 80 percent / nBu4NF*3H2O, HOAc / tetrahydrofuran / 48 h 6: 89 percent / H2 / 10percent Pd/C / ethyl acetate / 9 h View Scheme

1: 77 percent / LiBr, NEt3 / acetonitrile / 16 h / Ambient temperature 2: 80 percent / nBu4NF*3H2O, HOAc / tetrahydrofuran / 48 h 3: 89 percent / H2 / 10percent Pd/C / ethyl acetate / 9 h View Scheme

1: 80 percent / nBu4NF*3H2O, HOAc / tetrahydrofuran / 48 h 2: 89 percent / H2 / 10percent Pd/C / ethyl acetate / 9 h View Scheme