Benzyl Alcohol → Benzyl (4-methoxybicyclo[2.2.2]octan-1-yl)carbamate
Reaction equation
[CH3:1][O:2][C:3]12[CH2:10][CH2:9][C:6](C(O)=O)([CH2:7][CH2:8]1)[CH2:5][CH2:4]2.CC[N:16]([CH:20](C)C)C(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])C=CC=CC=1.[C:40]1([CH2:46][OH:47])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>O1CCOCC1>[CH2:46]([O:47][C:20](=[O:30])[NH:16][C:6]12[CH2:5][CH2:4][C:3]([O:2][CH3:1])([CH2:8][CH2:7]1)[CH2:10][CH2:9]2)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a solution of 4-methoxybicyclo[2.2.2]octane-1-carboxylic acid (5.9 g, 32 mmol) in dioxane (80 mL) was added DIEA (8.3 g, 64.2 mmol), diphenyl phosphoryl azide (13.2 g, 48 mmol) and phenylmethanol (17.3 g, 160 mmol). The mixture was stirred at 80° C. overnight and then concentrated under reduce pressure. The residue was purified by silica gel column chromatography (5% methanol in DCM) to give the desired product. (9 g, 31 mmol, yield 96%). MS (ESI) m/z=290.2 [M+H]+.
Workup
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (5% methanol in DCM)
Sources & evidence
- ORD record
- ord-728dfa57ac4249cebc8e34b6f1c275b2
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09139534B2
Reaction notes
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