Carisbamate → (R)-Carisbamate

Participants

Reaction Steps

(R)-1-o-Chlorophenyl-1,2-ethanediol carbonate was prepared using the same synthetic method described in Example 2, except that (S)-2-carbamoyloxy-1-o-chlorophenylethanol (10.98 g) was used instead of (D/L)-1-m-chlorophenyl-1,2-ethanediol. The crude (R)-2-carbamoyloxy-1-o-chlorophenylethanol prepared in this manner was used in the synthetic method described in Example 6 for (D/L)-1-m-chlorophenyl-1,2-ethanediol carbonate to yield (R)-2-carbamoyloxy-1-o-chlorophenylethanol (4.02 g, yield 54%). An analytically pure sample of (R)-2-carbamoyloxy-1-o-chlorophenylethanol ethanediol (3.35 g, yield 45%, m.p. 133° C., [α]D =-63.9 (c=2.22, methanol)) was obtained by recrystallization from ethyl acetate.

Provenance & Evidence