1: 1) n-BuLi / 1) THF, hexane, -70 deg C, 20 min, 2a) -70 deg C to RT, 2b) RT, 15 h 2: H2 / <(R)-(RuCl(p-cymene)BINAP>Cl / methanol; CH2Cl2 / 72 h / 50 °C / 37503 Torr 3: 97 percent / aq. HOAc / 3 h / 50 °C 4: 95 percent / tetramethylguanidine / tetrahydrofuran / 1) -70 to -30 deg C, 5 h, 2) -30 deg C, 2 d, 3) RT, 15 h 5: 85 percent / H2 / (R,R)-<Rh(1,5-COD)(DIPAMP)>BF4 / methanol; CH2Cl2 / 48 h / 2250.2 Torr / Ambient temperature 6: 6M HCl / dioxane; CH2Cl2 / 0.5 h / Ambient temperature 7: hydroxybenzotriazole, N-ethyl-N'-(3-dimethylaminopropyl)carbodiimide*HCl / CH2Cl2 / 15 h / -10 deg C to RT 8: 71 percent / HOAc / H2O / 4 h / 50 °C 9: 96 percent / Bu4NF*3H2O / dimethylformamide / 2 h / Ambient temperature 10: EDCI / CH2Cl2 / 15 h / -10 deg C to RT 11: 6M HCl / dioxane; CH2Cl2 / 0.5 h / Ambient temperature 12: aq. KHCO3 / CHCl3 / 1) RT, 2 h, 2) 50 deg C, 30 min 13: 95 percent / 1M LiOH / H2O; dioxane / 2 h / 10 °C 14: thioanisole, BrSiMe3, CF3COOH / 1 h / 0 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1848563', constants.ctx, '0')">N-(1-chloro-2-methylprop-1-enyl)-N,N-dimethylamine</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=0&deg;C;&nbsp;0.25&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>2: 90 percent / LiOH*H₂O / dioxane; H₂O / 1) RT, 5 h, ultrasound, 2) 50 deg C, 15 h<br />3: 1-chloro-1-(N,N-dimethylamino)-2-methyl-1-propene / CH₂Cl₂ / 0.25 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: 90 percent / LiOH*H₂O / dioxane; H₂O / 1) RT, 5 h, ultrasound, 2) 50 deg C, 15 h<br />2: 1-chloro-1-(N,N-dimethylamino)-2-methyl-1-propene / CH₂Cl₂ / 0.25 h / 0 &deg;C<br /> <br /> &nbsp;