Tetrabutylammonium Fluoride → HCID 58573730, compound

HRID 932202Notes

Reaction equation

HRID 932202 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([C:22]1([CH3:66])[CH2:27][C@H:26]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[C@@H:25]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=2)[N:24]([C@@H:42]([CH:62]2[CH2:64][CH2:63]2)[CH2:43][O:44][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[C:23]1=[O:65])[CH:20]=[CH2:21]>C1COCC1.C(OCC)(=O)C>[CH2:19]([C@@:22]1([CH3:66])[CH2:27][C@H:26]([C:28]2[CH:33]=[CH:32][CH:31]=[C:30]([Cl:34])[CH:29]=2)[C@@H:25]([C:35]2[CH:36]=[CH:37][C:38]([Cl:41])=[CH:39][CH:40]=2)[N:24]([C@@H:42]([CH:62]2[CH2:63][CH2:64]2)[CH2:43][OH:44])[C:23]1=[O:65])[CH:20]=[CH2:21]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67998609HCID 67998609, compound

Product 1

HCID 58573730HCID 58573730, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of tetrabutylammonium fluoride in THF (1M, 2.10 mL, 2.10 mmol) was added to a solution of diastereomers (5R,6S)-3-allyl-1-((S)-2-(tert-butyldiphenylsilyloxy)-1-cyclopropylethyl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methylpiperidin-2-one (Example 251, Step D, 488 mg, 0.700 mmol) in THF (10 ml).The reaction was stirred at ambient temperature for 2 hours. The mixture was diluted in ethyl acetate and washed with water and sat. aq. NaCl solution. The organic layer was dried over sodium sulfate. Silica gel chromatography eluting with ethyl acetate/hexane gave the title compound as a single diastereomer.

Workup

  1. washwashed with water and sat. aq. NaCl solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. washSilica gel chromatography eluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-2777cdb1b8444b5a82930f15c552382c
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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