Acetone → HCID 178457354, compound

Participants

Reaction Steps

Example 1 h, Step 1: A sample of (4-Amino-cyclohexyl)-carbamic acid tert-butyl ester (available from Albany Molecular Research; 2.00 g, 10.7 mmol, 1 eq.), acetone (1.18 mL, 16.1 mmol, 1.5 eq.), sodium triacetoxyborohydride (3.41 g, 16.1 mmol, 1.5 eq.) and 50 mL of methylene chloride were stirred at RT for 20 hours. Added 20 mL of 1 N NaOH and stirred 10 minutes then extracted 3× with methylene chloride. The organic layers were combined, dried and stripped in vacuo to obtain an oil. Added sodium triacetoxyborohydride (3.41 g, 16.1 mmol, 1.5 eq.) and 37% formaldehyde (aqueous) (2.62 mL, 32.2 mmol, 3 eq). Stirred 4 hours. Added 20 mL of 1 N NaOH and stirred 10 minutes then extracted the aqueous 3× with methylene chloride. The organic layers were combined, dried and stripped in vacuo to give cis-[4-(Isopropyl-methyl-amino)-cyclohexyl]-carbamic acid tert-butyl ester (3.20 g) as a colorless oil. MS found: (M+H)+=271.

Provenance & Evidence