tert-Butanol → tert-Butyl N-[1-(4-methoxyphenyl)cyclopropyl]carbamate
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2(C(O)=O)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:22])C=CC=CC=1.C([N:34]([CH2:37]C)CC)C.[CH3:39][C:40]([OH:43])([CH3:42])[CH3:41]>>[C:40]([O:43][C:37]([NH:34][C:9]1([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[CH2:10][CH2:11]1)=[O:22])([CH3:42])([CH3:41])[CH3:39]Participants
5
Procedure
A solution of 1-(4-methoxyphenyl)-1-cyclopropanecarboxylic acid (5.00 g, 26.0 mmol), diphenylphosphoryl azide (7.87 g, 28.6 mmol) and triethylamine (3.03 g, 29.9 mmol) in t-BuOH (50 ml) was heated at 100° C. for 24 h. After the solvent was evaporated in vacuo, the residue was diluted with CH2Cl2 -H2O. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was washed with 10% HCl aq., sat. NaHCO3 aq. and brine, dried (MgSO4) and concentrated in vacuo to give crude product (6.86 g) as a pale yellow solid. The crude product was recrystallized from hexane-ethyl acetate to give Compound 6 (4.98 g, 73%) as a white powder solid.
Workup
- customAfter the solvent was evaporated in vacuo
- additionthe residue was diluted with CH2Cl2 -H2O
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with CH2Cl2
- washThe combined solution was washed with 10% HCl aq., sat. NaHCO3 aq. and brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customto give crude product (6.86 g) as a pale yellow solid
- customThe crude product was recrystallized from hexane-ethyl acetate
Sources & evidence
- ORD record
- ord-6437828c72db49af845131698af5632a
- Source dataset
- uspto-grants-1998_08
- Patent number
- US05789423
Reaction notes
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