tert-Butanol → tert-Butyl cyclohex-3-en-1-ylcarbamate

Reaction equation

[CH:1]1(C(O)=O)[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1.C([N:12]([CH2:15]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.[C:34]([OH:38])([CH3:37])([CH3:36])[CH3:35]>>[C:34]([O:38][C:15]([NH:12][CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1)=[O:24])([CH3:37])([CH3:36])[CH3:35]

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 209033-Cyclohexene-1-carboxylic acid

HCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 11063381tert-Butyl cyclohex-3-en-1-ylcarbamate

Conditions

Temperature: 90 °C

Procedure

3-Cyclohexene-1-carboxylic acid (25.3 g) was dissolved in tert-butanol (250 ml), triethylamine (28 ml) and diphenylphosphorylazide (43.0 ml) were added, and the mixture was stirred for 1 hour at room temperature and 2 days at 90° C. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (dichloromethane) and then repurified by column chromatography on silica gel (hexane:ethyl acetate=20:1) to obtain the title compound (24.9 g) as colorless crystals.