Tert-Butylamine → HCID 69286066, compound

Participants

Reaction Steps

N-4-BOC-aminocyclohexanone (5.00 g, 23 mmol, 1 eq.), tert-butylamine (2.46 mL, 23 mmol, 1 eq.), and titanium (IV) isoproproxide (6.87 mL, 23 mmol, 1 eq.), were mixed and stirred at RT under nitrogen overnight. MeOH (50 mL) was added followed by NaBH4 pellets (0.89 g, 23 mmol, 1 eq.). After 30 minutes added 50 mL of 1 N NaOH. Methylene chloride was added, the insoluble matter filtered, and the layers separated. The aqueous layer was extracted twice more with methylene chloride. The organic layers were combined, dried and stripped to yield (4-tert-Butylamino-cyclohexyl)-carbamic acid tert-butyl ester (6.26 g) as an amber oil, which solidified upon standing. MS found: (M+H)+=271.

Provenance & Evidence