Benzyl Alcohol → benzyl tert-butyl ((1S,3S)-cyclopentane-1,3-diyl)dicarbamate
Reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:8])C=CC=CC=1.[C:18]([O:22][C:23]([NH:25][C@H:26]1[CH2:30][CH2:29][C@H:28](C(O)=O)[CH2:27]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].CC[N:36]([CH2:39]C)CC.[CH2:41]([OH:48])[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[C@H:28]1([NH:36][C:39](=[O:8])[O:48][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:29][CH2:30][C@H:26]([NH:25][C:23](=[O:24])[O:22][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:27]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
Diphenylphosphoryl azide (1.90 mL, 8.82 mmol) was added to a stirred mixture of (1S,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid (1.359 g, 5.93 mmol) and Et3N (1.65 mL, 11.84 mmol) in dry toluene (27.5 mL) and the resulting mixture was heated to 90° C. for 3 h. Benzyl alcohol (3.4 mL, 32.8 mmol) and DMAP (67 mg, 0.55 mmol) were added and the mixture was heated for an additional 16 h. The mixture was cooled and the solids were collected by filtration, rinsing with 1:1 toluene:hexane (4 mL), and dried to give the title compound as a white solid (1.649 g). The mother liquors were purified by silica gel chromatography (5% CH2Cl2, 10-80% EtOAc/hexane gradient), to give additional product (0.386 g). The combined solids are 88 area % pure at 215 nm; MS=235.3 (M+1-isobutylene and CO2).
Workup
- temperaturethe mixture was heated for an additional 16 h
- temperatureThe mixture was cooled
- filtrationthe solids were collected by filtration
- washrinsing with 1:1 toluene
- dry with materialhexane (4 mL), and dried
Sources & evidence
- ORD record
- ord-f4cb3b750168420a85636ee19526ec48
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07452893B2
Reaction notes
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