Water → (2S)-tert-butyl 4-hydroxy-2-(((triisopropylsilyl)oxy)methyl)piperidine-1-carboxylate

HRID 1522016Notes

Reaction equation

Cl[Si:2]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[CH:3]([CH3:5])[CH3:4].[OH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:15]([CH2:26][OH:27])[CH2:14]1.C(N(CC)CC)C.O>CN(C)C1C=CN=CC=1.ClCCl>[OH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[C@H:15]([CH2:26][O:27][Si:2]([CH:9]([CH3:11])[CH3:10])([CH:6]([CH3:8])[CH3:7])[CH:3]([CH3:5])[CH3:4])[CH2:14]1

Participants

Conditions

Temperature: 0 °C

Procedure

Chlorotriisopropylsilane (2.284 g, 11.85 mmol) was added dropwise to a 0° C. solution of Example 260A (2.65 g, 10.77 mmol), triethylamine (1.253 g, 12.39 mmol) and 4-(dimethylamino)pyridine (0.263 g, 2.154 mmol) in dichloromethane (25 mL). The mixture was stirred at 0° C. for 20 minutes and at room temperature for 16 hours. Water (50 mL) was added and the layers were separated. The aqueous layer was extracted with dichloromethane (twice), and the combined extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography on silica gel (gradient of 0-30% ethyl acetate/heptanes) to give the title compound as a mixture of diastereomers. MS (ESI+) m/z 388.0 (M+H)+.

Workup

customthe layers were separated
extractionThe aqueous layer was extracted with dichloromethane (twice), and the combined extracts
dry with materialwere dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by flash chromatography on silica gel (gradient of 0-30% ethyl acetate/heptanes)

Sources & evidence

ORD record: ord-7759fe11493e40b2931f5bc2accea829
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073922B2

Reaction notes

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