1-((Phenylmethoxy)carbonyl)-3-piperidinebutanoic acid → Phenylmethyl 3-(4-hydroxybutyl)-1-piperidinecarboxylate

HRID 2403827Notes

Reaction equation

[C:1]1([CH2:7][O:8][C:9]([N:11]2[CH2:16][CH2:15][CH2:14][CH:13]([CH2:17][CH2:18][CH2:19][C:20](O)=[O:21])[CH2:12]2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C1COCC1>[OH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH:13]1[CH2:14][CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:10])[CH2:12]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 4-(1-{[(phenylmethyl)oxy]carbonyl}-3-piperidinyl)butanoic acid (5.01 g, 16.41 mmol) in dry THF (40 ml) at 0° C. under nitrogen was added a solution of Borane-THF complex, (1M soln. in THF) (49.2 ml, 49.2 mmol), dropwise over 1 hour. The mixture was allowed to stir at 0° C. and gradually allowed to warm to rt over 20 hours. The mixture was cooled in an ice bath and cautiously quenched with dropwise addition of MeOH (20 ml) stirred in the cold bath for 2 hours then quenched further with 10% 2N HCl/MeOH (20 ml), stirred for 1 hour at rt and evaporated under reduced pressure. The residue was co-evaporated with methanol several times.

Workup

temperatureto warm to rt over 20 hours
temperatureThe mixture was cooled in an ice bath
customcautiously quenched with dropwise addition of MeOH (20 ml)
stirringstirred in the cold bath for 2 hours
customthen quenched further with 10% 2N HCl/MeOH (20 ml)
stirringstirred for 1 hour at rt
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-a5b01dad871642769e7300f04eefed21
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802684B2

Reaction notes

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