m-Chloroperbenzoic acid → N-tert-Butoxycarbonyl-[3-(7-oxa-bicyclo[4.1.0]hept-3-yl)-propyl]-carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:15][CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][CH:21]=[CH:20][CH2:19]1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])([CH3:4])([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:33])C=1>>[C:11]([O:10][C:8](=[O:9])[N:7]([CH2:15][CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][CH:21]2[CH:20]([O:33]2)[CH2:19]1)[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:24])([CH3:14])([CH3:13])[CH3:12]Participants
3
Procedure
N-tert-Butoxycarbonyl-(3-cyclohex-3-enyl-propyl)-carbamic acid tert-butyl ester (12.2 g, 29.4 mmol, corrected) was treated with 3-chloroperbenzoic acid (70% purity, 8.7 g, 35.3 mmol, corrected) according to the method of Example 7 Step B and stirred at room temperature for 4.5 hours. After work up the title compound (9.38 g, 90% yield) was obtained as light yellow oil.
Sources & evidence
- ORD record
- ord-67c80d31658f4c1c919eb40920b0fc61
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08071643B2
Reaction notes
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