Sodium hydride → HCID 18723402, compound

HRID 522927Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[H-].[Na+].Br[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=1>CN(C=O)C>[F:27][C:26]([F:28])([F:29])[O:25][C:22]1[CH:23]=[CH:24][C:19]([CH2:18][O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (1 g, 4.97 mmol) in DMF (15 mL, 3 mL/mmol) was added sodium hydride (143 mg, 5.95 mmol). After being stirred for 0.5 h at 0° C. 1-(bromomethyl)-4-(trifluoromethoxy)benzene (1.9 g, 7.97 mmol) was added and the reaction was stirred for 24 h at RT. The reaction was quenched with water and extracted with EtOAc (2×20 mL). The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure and purified by silica gel column chromatography to give tert-butyl 4-(4-(trifluoromethoxy)benzyloxy)piperidine-1-carboxylate (1.8 g) which was taken to the next reaction without further purification. Observed mass (M+1): 376.

Workup

stirringthe reaction was stirred for 24 h at RT
customThe reaction was quenched with water
extractionextracted with EtOAc (2×20 mL)
washThe organic extracts were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
custompurified by silica gel column chromatography

Sources & evidence

ORD record: ord-651600afe829421e96b98cab1d769765
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334269B2

Reaction notes

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