Water → Tert-butyl 4-(4-chlorophenyl)-4-hydroxymethylpiperidine-1-carboxylate

HRID 556953Notes

Reaction equation

C[O:2][C:3]([C:5]1([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>CCOCC>[C:14]([O:13][C:11]([N:8]1[CH2:7][CH2:6][C:5]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)([CH2:3][OH:2])[CH2:10][CH2:9]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

To a chilled solution of 4-(4-chloro-phenyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-methyl ester (700 mg, 1.98 mmol) in 6 ml ether was added dropwise 2 ml lithium aluminium hydride 1M solution in ether. The reaction was stirred at 0° C. for 3 hours, then water (100 ml) was slowly added. The resulting gel was filtered and the aqueous filtrate was extracted three times with ether. The combined organic layers were dried with magnesium sulfate and concentrated under vacuum. Recovered oil was purified by silica gel chromatography, eluting with hexane-ethyl acetate (6:4) to give the title compound (297 mg, 46%).

Workup

filtrationThe resulting gel was filtered
extractionthe aqueous filtrate was extracted three times with ether
dry with materialThe combined organic layers were dried with magnesium sulfate
concentrationconcentrated under vacuum
customRecovered oil
customwas purified by silica gel chromatography
washeluting with hexane-ethyl acetate (6:4)

Sources & evidence

ORD record: ord-17e41b55145240c79e69f4e05a7d36a3
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058287B2

Reaction notes

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