tert-Butanol → Tert-butyl 2-(4-chlorophenyl)cyclopropylcarbamate
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][CH:9]2C(O)=O)=[CH:4][CH:3]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:21])C=CC=CC=1.C([N:33]([CH2:36]C)CC)C.[CH3:38][C:39]([OH:42])([CH3:41])[CH3:40]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:10][CH:9]2[NH:33][C:36](=[O:21])[O:42][C:39]([CH3:41])([CH3:40])[CH3:38])=[CH:6][CH:7]=1Participants
5
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 2-(4-chlorophenyl)cyclopropanecarboxylic acid (100 mg, 0.509 mmol), diphenylphosphoryl azide (0.1209 ml, 0.559 mmol), triethylamine (0.106 ml, 0.763 mmol), and t-BuOH (2 ml) was heated at 90° C. under nitrogen atmosphere 17 hours. The mixture was concentrated, diluted with EtOAc (20 ml), and washed with saturated K2CO3 solution (10 ml). The EtOAc layer was dried over MgSO4, filtered, concentrated, and dried under high vacuum for 17 hours to provide 300 mg of a light brown solid. The crude solid was purified on silica gel (EtOAc in hexanes gradient) to provide 64.7 mg of the title compound as a solid (47.5%).
Workup
- concentrationThe mixture was concentrated
- additiondiluted with EtOAc (20 ml)
- washwashed with saturated K2CO3 solution (10 ml)
- dry with materialThe EtOAc layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
- customdried under high vacuum for 17 hours
Sources & evidence
- ORD record
- ord-c71e733ab7ef4681b35f601606b494ac
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569522B2
Reaction notes
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