Tetrabutylammonium Fluoride → HCID 178519417, compound

HRID 1160261Notes

Reaction equation

HRID 1160261 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([N:41]3[CH2:46][CH2:45][CH:44]([C:47]([F:50])([F:49])[F:48])[CH2:43][CH2:42]3)=[O:40])=[CH:35][CH:34]=2)[CH:5]=[C:6]([Cl:32])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([O:20][Si](C(C)C)(C(C)C)C(C)C)[CH2:16][CH2:15]2)[C:10]1=[O:31].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[Cl:32][C:6]1[CH:5]=[C:4]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([N:41]3[CH2:46][CH2:45][CH:44]([C:47]([F:49])([F:48])[F:50])[CH2:43][CH2:42]3)=[O:40])=[CH:35][CH:34]=2)[CH:3]=[C:2]([Cl:1])[C:7]=1[CH2:8][C@@H:9]1[CH2:13][CH2:12][N:11]([C@H:14]2[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16][CH2:15]2)[C:10]1=[O:31]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178460985HCID 178460985, compound

Product 1

HCID 178519417HCID 178519417, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mix (R)-3-[3,5-Dichloro-4′-(4-trifluoromethyl-piperidine-1-carbonyl)-biphenyl-4-ylmethyl]-trans-1-(4-triisopropylsilanyloxy-cyclohexyl)-pyrrolidin-2-one (Preparation 22) (0.548 g, 0.78 mmol) and TBAF (1.55 ml, 1.55 mmol) in 15 ml of dry THF. Stir at room temperature for 2 hours. Quench with saturated NaHCO3 extract with ethyl acetate. Wash with brine. Dry over magnesium sulfate, filter, and concentrate. After flash column chromatography receive 0.448 g (97%) of the title compound: Mass spectrum (apci) m/z=596 (M+H).

Workup

  1. customQuench with saturated NaHCO3
  2. extractionextract with ethyl acetate
  3. washWash with brine
  4. dry with materialDry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-23c0d3d8a2c0454c8b922d39ca235f39
Source dataset
uspto-grants-2010_10
Patent number
US07816349B2

Reaction notes

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