Water → 2-(1-Benzyl-4-pyrrolidine-1-ylpiperidine-4-yl)ethanol

HRID 420597Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9](=O)[CH2:10][C:11]1([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:16][CH2:15][N:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1.O.[OH-].[Na+]>O1CCCC1>[CH2:17]([N:14]1[CH2:13][CH2:12][C:11]([CH2:10][CH2:9][OH:8])([N:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:16][CH2:15]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminium hydride (324 mg) was suspended in tetrahydrofuran (25 mL). A solution of (1-benzyl-4-pyrrolidine-1-ylpiperidine-4-yl)acetic acid methyl ester (2.70 g) in tetrahydrofuran (25 mL) was added thereto at 0° C. After stirring at 0° C. for 1 hour, to the reaction solution were sequentially added with water (0.35 mL), 10% aqueous sodium hydroxide (0.35 mL) and water (1.05 mL). The insoluble material was filtrated and the filtrate was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over sodium sulphate. The solvent was evaporated under reduced pressure to give the title compound. The obtained objective substance was provided to the next reaction without further purification.

Workup

customat 0° C
filtrationThe insoluble material was filtrated
extractionthe filtrate was extracted with ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over sodium sulphate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-dc0b0ac85b6b4d869036be129fc3bf47
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08097610B2

Reaction notes

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