Tetrabutylammonium Fluoride → HCID 68914570, compound

HRID 732646Notes

Reaction equation

HRID 732646 reaction equation
[Si]([O:8][CH2:9][C@@H:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH2:13][N:12]([C:25](=[O:40])[CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:11]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][CH2:9][C@@H:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH2:13][N:12]([C:25](=[O:40])[CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:31])[CH2:11]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 68910560HCID 68910560, compound

Product 1

HCID 68914570HCID 68914570, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Benzyl 6-{(3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-[3-(trifluoromethyl)phenyl]pyrrolidin-1-yl}-6-oxohexanoate was dissolved in THF, mixed with a THF solution of TBAF at room temperature and stirred for 5Hours. Thereafter, work-up and purification were carried out in the standard method to obtain benzyl 6-{(3R,4S)-3-(hydroxymethyl)-4-[3-(trifluoromethyl)phenyl]pyrrolidin-1-yl}-6-oxohexanoate.

Workup

  1. customThereafter, work-up and purification

Sources & evidence

ORD record
ord-0b00d7f0e01648e9834ad3af7617240e
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

Loading…