(Trifluoromethyl)trimethylsilane → HCID 86668887, compound

HRID 1524647Notes

Reaction equation

HRID 1524647 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@:8]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C@H:12]([CH:13]=[O:14])[C@@H:11]([CH3:15])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C[Si](C)(C)[C:26]([F:29])([F:28])[F:27].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:5][C:6](=[O:23])[NH:7][C@:8]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C@H:12]([CH:13]([OH:14])[C:26]([F:29])([F:28])[F:27])[C@@H:11]([CH3:15])[O:10][CH2:9]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 86668886HCID 86668886, compound

Product 1

HCID 86668887HCID 86668887, compoundYield 492%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

[(3S,4S,5R)-3-(2-Fluoro-phenyl)-4-formyl-5-methyl-tetrahydro-furan-3-yl]-carbamic acid tert-butyl ester (Preparation Example 30-(2)) (2.00 g, 0.62 mmol) dissolved in THF (20 mL). Trimethyl(trifluoromethyl) silane (175.89 mg, 1.23 mmol) was added followed by TBAF (0.080 g, 0.30 mmol). The reaction mixture was stirred at RT and monitored by LCMS (Agilent Method A), retention time 5.61 min (MH+ 294). The reaction went to completion after 2 h. The reaction was then concentrated, saturated aqueous ammonium chloride (10 ml) was added and extracted with DCM (2×20 ml). The combined organic phases were combined, dried over MgSO4 concentrated and purified by flash chromatography (Hexane/EtOAc 5-40%). 1.20 g (49% yield) of the title compound was isolated as a mixture of the 2 epimers (85/15).

Workup

  1. concentrationThe reaction was then concentrated
  2. additionsaturated aqueous ammonium chloride (10 ml) was added
  3. extractionextracted with DCM (2×20 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography (Hexane/EtOAc 5-40%)

Sources & evidence

ORD record
ord-1fcb6d7835dc45e98aa31b442e47563f
Source dataset
uspto-grants-2015_07
Patent number
US09079914B2

Reaction notes

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