Tetrabutylammonium Fluoride → HCID 58573730, compound

HRID 1048516Notes

Reaction equation

HRID 1048516 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-935af7133ca84bf6a7e7bd692a56243f
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

Loading…