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

HRID 2104365Notes

Reaction equation

HRID 2104365 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](=[O:24])[NH:12][CH:1]1[CH2:6][CH2:5][CH:4]=[CH:3][CH2:2]1)([CH3:37])([CH3:36])[CH3:35]

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

Procedure

3-Cyclohexene-1-carboxylic acid (25.3 g) was dissolved in tert-butanol (250 mL), and to the solution were added triethylamine (28 mL) and diphenylphosphoryl azide (43.0 mL), followed by stirring at room temperature for 1 hour, and then at 90° C. for 2 days. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride). The purified product was further purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to thereby give the title compound (24.9 g).

Workup

  1. waitat 90° C. for 2 days
  2. distillationThe solvent was distilled away under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (methylene chloride)
  4. customThe purified product was further purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-51145d56c27c40109465b1f0fb4f4a00
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

Loading…