(Trifluoromethyl)trimethylsilane → HCID 71152236, compound

HRID 1481611Notes

Reaction equation

HRID 1481611 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:17]([CH:18]=[O:19])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:20]([CH3:22])[CH3:21])[S:14]2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si]([C:27]([F:30])([F:29])[F:28])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.C([O-])(O)=O.[Na+]>[CH2:1]([O:8][C@@H:9]1[C@@H:17]([CH:18]([OH:19])[C:27]([F:30])([F:29])[F:28])[O:16][C@H:15]2[C@H:11]([N:12]=[C:13]([N:20]([CH3:22])[CH3:21])[S:14]2)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium Fluoride2×HCID 88541262HCID 88541262, compound

Product 1

HCID 71152236HCID 71152236, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of (3aR,5S,6S,7aR)-6-(benzyloxy)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-5-carbaldehyde (0.650 g) in anhydrous THF (15 mL) at room temperature was TMSCF3 (0.750 mL, 5.08 mmol) followed by TBAF (1.0 M in THF, 0.10 mL, 0.10 mmol). The reaction was stirred at room temperature for 2 h. Another 2.50 mL of TBAF (1.0 M in THF) was added and the mixture was stirred at room temperature for 18 h. The solution was diluted with saturated aqueous NaHCO3 (30 mL), extracted with EtOAc (2×20 mL). The combined extract was dried over anhydrous Na2SO4. The solvents were evaporated under reduced pressure, and the residue was purified by silica gel column chromatography, eluted with 1%-3% 2 M NH3 MeOH solution in DCM to give 1-((3aR,5R,6S,7aR)-6-(benzyloxy)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)-2,2,2-trifluoroethanol (0.274 g, 35%) as a pale yellow foam. MS m/z 391.1 (M+1, 100%). An estimation ratio of the two diastereomers was 70:30 based on its 1H NMR (400 MHz, CDCl3) spectrum.

Workup

  1. customat room temperature
  2. stirringthe mixture was stirred at room temperature for 18 h
  3. extractionextracted with EtOAc (2×20 mL)
  4. extractionThe combined extract
  5. dry with materialwas dried over anhydrous Na2SO4
  6. customThe solvents were evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography
  8. washeluted with 1%-3% 2 M NH3 MeOH solution in DCM

Sources & evidence

ORD record
ord-c10330c938e04156b684980ee974b664
Source dataset
uspto-grants-2016_08
Patent number
US09409924B2

Reaction notes

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