(Trifluoromethyl)trimethylsilane → HCID 68000038, compound

HRID 932085Notes

Reaction equation

HRID 932085 reaction equation
[CH2:1]([C@@:4]1([CH3:31])[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]([CH2:28][CH3:29])[CH2:25][CH:26]=[O:27])[C:5]1=[O:30])[CH:2]=[CH2:3].C[Si](C)(C)[C:34]([F:37])([F:36])[F:35].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([C@@:4]1([CH3:31])[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]([CH2:25][CH:26]([OH:27])[C:34]([F:37])([F:36])[F:35])[CH2:28][CH3:29])[C:5]1=[O:30])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 86660730HCID 86660730, compound

Product 1

HCID 68000038HCID 68000038, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (S)-3-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)pentanal (100 mg, 0.218 mmol; Example 130, Step A) in THF (2.2 mL) was added trimethyl(trifluoromethyl)silane (97 μL, 0.66 mmol) at 0° C. and the reaction was stirred for 5 min. Then 1 M TBAF in THF (327 μL, 0.327 mmol) was added slowly at 0° C. After being stirred at 0° C. for 40 min, the reaction was quenched (sat. aq. NaCl solution), extracted (2×EtOAc), and washed (sat. aq. NaCl solution). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure. Purification of the residue by chromatography on silica gel (12 g SiO2, 13% and 23% EtOAc/Hex) provided the title compound as a mixture of two diastereomers.

Workup

  1. stirringAfter being stirred at 0° C. for 40 min
  2. customthe reaction was quenched (sat. aq. NaCl solution)
  3. extractionextracted (2×EtOAc)
  4. washwashed (sat. aq. NaCl solution)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification of the residue by chromatography on silica gel (12 g SiO2, 13% and 23% EtOAc/Hex)

Sources & evidence

ORD record
ord-87390b816dff45f7aaad3974f5db2b4d
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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