Tetrabutylammonium Fluoride → (R)-tert-butyl 3-((S)-1-(3-chlorophenyl)-1,5-dihydroxypentyl)piperidine-1-carboxylate

HRID 451669Notes

Reaction equation

[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][C@:13]([C@@H:22]1[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]1)([C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:21])[CH:16]=1)[OH:14])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>CC#N>[Cl:21][C:17]1[CH:16]=[C:15]([C@:13]([C@@H:22]2[CH2:27][CH2:26][CH2:25][N:24]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:23]2)([OH:14])[CH2:12][CH2:11][CH2:10][CH2:9][OH:8])[CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (R)-tert-butyl 3-((S)-5-(tert-butyldimethylsilyloxy)-1-(3-chlorophenyl)-1-hydroxypentyl)piperidine-1-carboxylate (511 mg, 1 mmol) in CH3CN (10 mL) was added tetrabutylammonium fluoride (550 mg, 2 mmol) in one portion. The reaction mixture was stirred at 60° C. for 2 h. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel with EtOAc/hexane to give (R)-tert-butyl 3-((S)-1-(3-chlorophenyl)-1,5-dihydroxypentyl)piperidine-1-carboxylate (350 mg, 80%). 1H NMR (400 MHz, CDCl3): 1.05-1.42 (m, 6H), 1.46 (s, 9H), 1.52-1.79 (m, 4H), 1.94-2.03 (m, 2H), 2.55 (m, 2H), 3.56 (m, 2H), 3.97 (m, 1H), 4.36 (m, 1H), 7.20-7.25 (m, 3H), 7.37 (s, 1H). MS (E/Z): 398 (M+H+)

Workup

customThe solvent was removed under reduced pressure
customThe residue was purified by column chromatography on silica gel with EtOAc/hexane

Sources & evidence

ORD record: ord-6083c60a64ee4f4bbf2496750172b4b0
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487108B2

Reaction notes

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