Carbamic acid, (3-hydroxycyclopentyl)-, 1,1-dimethylethyl ester, (1S-trans)-

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (1S-trans)-[3-(formyloxy)cyclopentyl]carbamic acid 1,1-dimethylethyl ester (0.081 g, 0.35 mmol) in methanol (3 ml) was treated with a slurry of potassium hydrogen carbonate (0.707 g, 7.06 mmol) in water (1.5 ml) and stirred at room temperature for 2h. The mixture was then diluted with water (20 ml) and ethyl acetate (20 ml) and the aqueous phase was extracted with ethyl acetate (2×20 ml). The combined organic phase was dried (MgSO4) and evaporated to leave a solid which was purified by column chromatography on flash silica eluting with 30-40% ethyl acetate in cyclohexane to give the title compound (0.037 g) from diisopropyl ether m.p. 83-85° C., [α]D 0.0° (CHCl3 c=0.55%). the aqueous phase was extracted with ethyl acetate (2×20 ml) The combined organic phase was dried (MgSO4) evaporated to leave a solid which was purified by column chromatography on flash silica eluting with 30-40% ethyl acetate in cyclohexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The trans-(3-hydroxy-cyclopentyl)-carbamic acid tert-butyl ester was converted to cis-(3-amino-cyclopentyl)-carbamic acid tert-butyl ester using the same method described previously. The resulting compound was further converted to cis-[3-(2,5-dimethyl-benzoimidazol-1-yl)-cyclopentyl]-carbamic acid tert-butyl ester using the same method described in the preparation of the hydrochloride salt of trans-3-(2,5-dimethyl-benzoimidazol-1-yl)-cyclopentylamine. After the acid cleavage of the carbamic acid tert-butyl ester and base extraction, cis-3-(2,5-dimethyl-benzoimidazol-1-yl)-cyclopentylamine was obtained as pale brown oil. LR-MS calcd for C14H19N3 (m/e) 229.1579, obsd 230.2 (M+H). After the acid cleavage of the carbamic acid tert-butyl ester and base extraction

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (1S-trans)-[3-(formyloxy)cyclopentyl]carbamic acid 1,1-dimethylethyl ester (0.081 g, 0.35 mmol) in methanol (3 ml) was treated with a slurry of potassium hydrogen carbonate (0.707 g, 7.06 mmol) in water (1.5 ml) and stirred at room temperature for 2 h. The mixture was then diluted with water (20 ml) and ethyl acetate (20 ml) and the aqueous phase was extracted with ethyl acetate (2×20 ml). The combined organic phase was dried (MgSO4) and evaporated to leave a solid which was purified by column chromatography on flash silica eluting with 30-40% ethyl acetate in cyclohexane to give the title compound (0.037 g) from diisopropyl ether m.p. 83°-85° C., [α]D 0.0° (CHCl3 c=0.55%). the aqueous phase was extracted with ethyl acetate (2×20 ml) The combined organic phase was dried (MgSO4) evaporated to leave a solid which was purified by column chromatography on flash silica eluting with 30-40% ethyl acetate in cyclohexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (1S-trans)-[3-(formyloxy)cyclopentyl]carbamic acid 1,1-dimethylethyl ester (0.081 g, 0.35 mmol) in methanol (3 ml) was treated with a slurry of potassium hydrogen carbonate (0.707 g, 7.06 mmol) in water (1.5 ml) and stirred at room temperature for 2h. The mixture was then diluted with water (20 ml) and ethyl acetate (20 ml) and the aqueous phase was extracted with ethyl acetate (2×20 ml). The combined organic phase was dried (MgSO4) and evaporated to leave a solid which was purified by column chromatography on flash silica eluting with 30-40% ethyl acetate in cyclohexane to give the title compound (0.037 g) from diisopropyl ether m.p. 83-85° C., [α]D 0.0° (CHCl3 c=0.55%). the aqueous phase was extracted with ethyl acetate (2×20 ml) The combined organic phase was dried (MgSO4) evaporated to leave a solid which was purified by column chromatography on flash silica eluting with 30-40% ethyl acetate in cyclohexane