Borane;tetrahydrofuran → (2S)-tert-butyl 4-Hydroxy-2-(hydroxymethyl)piperidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][C@H:9]1[C:15](O)=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.O1CCCC1>O1CCCC1>[OH:14][CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C@H:9]([CH2:15][OH:16])[CH2:10]1Participants
Procedure
A solution of (S)-1-(tert-butoxycarbonyl)-4-oxopiperidine-2-carboxylic acid (5 g, 20.55 mmol) in tetrahydrofuran (100 mL) under nitrogen was cooled in an ice bath. 1N Borane-tetrahydrofuran in tetrahydrofuran (61.7 mL, 61.7 mmol) was added dropwise over 25 minutes and the mixture was stirred at room temperature for 3 hours, cooled to 0° C. and quenched with 10 mL water. Potassium carbonate (5 g) was added and the mixture was stirred overnight at room temperature, and partitioned between water and ether (three times). The ether extracts were dried over sodium sulfate, filtered, concentrated onto silica gel, and purified by flash chromatography (gradient of 0-100% ethyl acetate-heptanes) to give the title compound as a mixture of diastereomers. MS (ESI+) m/z 231.9 (M+H)+.
Workup
- temperaturecooled to 0° C.
- customquenched with 10 mL water
- additionPotassium carbonate (5 g) was added
- stirringthe mixture was stirred overnight at room temperature
- custompartitioned between water and ether (three times)
- dry with materialThe ether extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated onto silica gel
- custompurified by flash chromatography (gradient of 0-100% ethyl acetate-heptanes)
Sources & evidence
- ORD record
- ord-c8eab40d38464c76a281a255793ca1c1
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073922B2
Reaction notes
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