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

HRID 902849Notes

Reaction equation

HRID 902849 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]>>[CH:1]1([NH:12][C:15](=[O:24])[O:38][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 209033-Cyclohexene-1-carboxylic acidHCID 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 (methylene chloride) and then repurified by column chromatography on silica gel (hexane:ethyl acetate=20:1) to obtain the title compound (24.9 g).

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel (methylene chloride)
  3. customrepurified by column chromatography on silica gel (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-e94fb2062ed34f5197512518284b633e
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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