Tetrabutylammonium Fluoride → HCID 86628523, compound

HRID 732621Notes

Reaction equation

HRID 732621 reaction equation
[Si]([O:8][CH2:9][C@@H:10]1[C@@H:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][N:12]([C:21](=[O:26])[C:22]([F:25])([F:24])[F:23])[CH2:11]1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:15]1([C@H:14]2[CH2:13][N:12]([C:21](=[O:26])[C:22]([F:24])([F:25])[F:23])[CH2:11][C@@H:10]2[CH2:9][OH:8])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86628522HCID 86628522, compound

Product 1

HCID 86628523HCID 86628523, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 11.9 g portion of (3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenyl-1-(trifluoroacetyl)pyrrolidine was dissolved in 30 ml of THF, and a THF solution of TBAF (1.0 M, 37 ml) was added thereto at room temperature and stirred for 2Hours. The reaction solution was concentrated under a reduced pressure, and the residue was mixed with water, extracted with diethyl ether and washed with water and saturated brine in that order. The organic layer was dried with anhydrous sodium sulfate and concentrated under a reduced pressure. The thus obtained residue was purified by a silica gel column chromatography (chloroform-ethyl acetate) to obtain 6.28 g of [(3R,4S)-4-phenyl-1-(trifluoroacetyl)pyrrolidin-3-yl]methanol as a yellow amorphous substance. FP: 274.

Workup

  1. concentrationThe reaction solution was concentrated under a reduced pressure
  2. additionthe residue was mixed with water
  3. extractionextracted with diethyl ether
  4. washwashed with water and saturated brine in that order
  5. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe thus obtained residue was purified by a silica gel column chromatography (chloroform-ethyl acetate)

Sources & evidence

ORD record
ord-14744fc368fb4df7b1c66b8fefdf88b5
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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