Water → tert-Butyl 4-(2-hydroxyethyl)-4-(hydroxymethyl)piperidine-1-carboxylate

HRID 852683Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[O:11]=[C:12]1[C:16]2([CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]2)[CH2:15][CH2:14][O:13]1.O>ClCCl>[OH:13][CH2:14][CH2:15][C:16]1([CH2:12][OH:11])[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: -78 °C

Procedure

Diisobutylaluminium hydride (1.0M in dichloromethane, 3.60 mL, 3.60 mmol) was added over 10 minutes to a stirred, cooled (−78° C.) solution of 1,1-dimethylethyl 1-oxo-2-oxa-8-azaspiro[4.5]decane-8-carboxylate (Description 23, 400 mg, 1.57 mmol) in dichloromethane (4 mL) and the mixture stirred at −78° C. for 3 hours, then at 0° C. for 2 hours. Water (1.6 mL) was added very slowly at 0° C. and the mixture was warmed to room temperature and stirred overnight. The mixture was filtered through Hyflo™, washing with dichloromethane, and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate, to give the title compound (255 mg, 63%). m/z (ES+) 260 (M+1).

Workup

waitat 0° C. for 2 hours
temperaturethe mixture was warmed to room temperature
stirringstirred overnight
filtrationThe mixture was filtered through Hyflo™
washwashing with dichloromethane
customthe solvent was evaporated under reduced pressure
customThe residue was purified by flash column chromatography on silica gel
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-5974a0688a9943cb85161f12ac40f8e4
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07253205B2

Reaction notes

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