Nitrogen → N-(5-(hydroxymethyl)bicyclo[3.2.1]octan-1-yl)acetamide
Reaction equation
C([O:8][C:9]([NH:11][C:12]12[CH2:19][C:16]([C:20]([O:22]C)=O)([CH2:17][CH2:18]1)[CH2:15][CH2:14][CH2:13]2)=O)C1C=CC=CC=1.[Li+].[BH4-].N#N.[CH2:28]1COCC1>>[OH:22][CH2:20][C:16]12[CH2:19][C:12]([NH:11][C:9](=[O:8])[CH3:28])([CH2:18][CH2:17]1)[CH2:13][CH2:14][CH2:15]2Participants
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of methyl 5-(benzyloxycarbonylamino)bicyclo[3.2.1]octane-1-carboxylate (1.0 g, 3.15 mmol) in THF (20 mL) at 0° C. was added LiBH4 (2M in THF, 3 mL, 6 mmol) dropwise under N2. After stirring at 0° C. for 30 min, the reaction was allowed to warm up to room temperature overnight. The reaction was quenched with Sat. NH4Cl and resulting mixture was extracted with ethyl acetate (3×20 mL). Combined organic phase was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford a residue, which was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3/1) to give 750 mg (81%) of the title compound, N-(5-(hydroxymethyl)bicyclo[3.2.1]octan-1-yl)acetamide as a colorless oil. ESI-MS m/z: 290 (M+H)+
Workup
- temperatureto warm up to room temperature overnight
- customThe reaction was quenched with Sat. NH4Cl
- customresulting mixture
- extractionwas extracted with ethyl acetate (3×20 mL)
- washCombined organic phase was washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customto afford a residue, which
- customwas purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3/1)
Sources & evidence
- ORD record
- ord-75a496413aad4cb2b3d5a299f678c8f3
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09212165B2
Reaction notes
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