N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2) → Benzyl 4-(3-fluoro-2-hydroxypropoxy)piperidine-1-carboxylate

HRID 2368106Notes

Reaction equation

HRID 2368106 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1.CCCC[N+](CCCC)(CCCC)CCCC.[FH:39].F.[F-]>>[F:39][CH2:3][CH:2]([OH:1])[CH2:4][O:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:13])[CH2:8][CH2:7]1

Participants

3

Reactant 2

HCID 11748636N,N,N-Tributylbutan-1-aminium fluoride--hydrogen fluoride (1/1/2)HCID 57517497Benzyl 4-(oxiran-2-ylmethoxy)piperidine-1-carboxylate

Product 1

HCID 67449609Benzyl 4-(3-fluoro-2-hydroxypropoxy)piperidine-1-carboxylateYield 49.6%

Conditions

Temperature
120 °C

Procedure

A mixture of benzyl 4-(oxiran-2-ylmethoxy)piperidine-1-carboxylate (1.81 g) and tetrabutylammonium dihydrogen trifluoride (3.74 g) was stirred at 120° C. overnight. The reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (960 mg).

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-023ef5c070954373bd9b5b3363bd4a00
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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