Dimethylamine → (1S-trans)-[3-(N,N-Dimethylamino)cyclopentyl]carbamic acid 1,1-dimethylethyl ester

関与物質

反応手順

(1S-cis)-[3-[(Methylsulphonyl)oxy]cyclopentyl]carbamic acid 1,1-dimethylethyl ester (1.452 g, 5.20 mmol) in a solution of dimethylamine (33% in ethanol, 25 ml) was heated at reflux for 3.75 h, then allowed to cool. The solution was diluted with water (100 ml) and extracted with ethyl acetate(3×100 ml). The total organic solution was dried (Na2SO4) and evaporated to a yellow gum. This was purified on silica, eluting with dichloromethane:ethanol:0.88 ammonia (100:8:1) changing to (30:8:1) to give a brown film (0.988 g, 83%). A portion of this was evaporated from a solution in isopropyl ether to give the title compound (0.139 g) as a brown solid, m.p. 65°-67° C., [α]D -40.35°(CHCl3 c=0.57%).

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