Tetrabutylammonium Fluoride → HCID 68000387, compound

HRID 932166Notes

Reaction equation

HRID 932166 reaction equation
[CH2:1]([C@@:4]1([CH3:41])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@H:24]([CH:27]([OH:39])[CH2:28][CH2:29][CH2:30][O:31][Si](C(C)(C)C)(C)C)[CH2:25][CH3:26])[C:5]1=[O:40])[CH:2]=[CH2:3].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:1]([C@@:4]1([CH3:41])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[N:6]([C@H:24]([CH:27]([OH:39])[CH2:28][CH2:29][CH2:30][OH:31])[CH2:25][CH3:26])[C:5]1=[O:40])[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67998721HCID 67998721, compound

Product 1

HCID 68000387HCID 68000387, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3S,5R,6S)-3-allyl-1-((3S)-7-(tert-butyldimethylsilyloxy)-4-hydroxyheptan-3-yl)-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methylpiperidin-2-one (127 mg, 0.21 mmol; Example 221, Step A) in THF (1.5 mL) was treated with tetrabutylammonium fluoride (0.62 mL 1M in THF, 0.62 mmol) at ambient temperature for 1.5 hours. The solvent was removed under vacuum. Purification by silica chromatography eluting with ethyl acetate/hexane provided the title compound as a mixture of diastereomers.

Workup

  1. customThe solvent was removed under vacuum
  2. customPurification by silica chromatography
  3. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-1b2a649ea031425087c89b6e31c81c2d
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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