Borane → HCID 117871296, compound

HRID 530582Notes

Reaction equation

HRID 530582 reaction equation
B.[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][CH2:13][C:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[C:18]([C:23]([F:26])([F:25])[F:24])[CH:17]=2)=[O:15])(=[O:11])=[O:10])=[CH:5][CH:4]=1>C1COCC1>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C@@H:14]([OH:15])[CH2:13][O:12][S:9]([C:6]2[CH:7]=[CH:8][C:3]([CH3:2])=[CH:4][CH:5]=2)(=[O:10])=[O:11])=[CH:17][C:18]=1[C:23]([F:26])([F:24])[F:25]

Participants

4

Reactant 2

HCID 6331BoraneHCID 117871851HCID 117871851, compound

Product 1

HCID 117871296HCID 117871296, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of (R)-(3aR)-tetrahydro-1-methyl-3,3-diphenyl-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborole (295 mg, 1.06 mmol) in THF (10 mL) was added borane in THF (1M, 11 mL, 11 mmol). The resulting solution was stirred and 2-(4-fluoro-3-(trifluoromethyl)phenyl)-2-oxoethyl 4-methylbenzenesulfonate (4.0 g, 10.6 mmol) in THF (30 mL) was added through a dropping funnel over 45 min. The solution was stirred at room temperature for 45 min. The mixture was quenched with methanol (5 mL) and concentrated. The resulting residue was extracted with ethyl acetate and 0.5N hydrochloric acid. The organic layer was dried and concentrated to give toluene-4-sulfonic acid (R)-2-(4-fluoro-3-trifluoromethyl-phenyl)-2-hydroxyethyl ester (3.85 g). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.46 (s, 3H) 3.99-4.19 (m, 2H) 5.03 (dd, J=8.08, 3.54 Hz, 1H) 7.11-7.22 (m, 1H) 7.35 (dd, J=8.59, 0.76 Hz, 2H) 7.49-7.55 (m, 1H) 7.57 (dd, J=6.69, 1.89 Hz, 1H) 7.76 (d, J=8.34 Hz, 2H).

Workup

  1. stirringThe solution was stirred at room temperature for 45 min
  2. customThe mixture was quenched with methanol (5 mL)
  3. concentrationconcentrated
  4. extractionThe resulting residue was extracted with ethyl acetate and 0.5N hydrochloric acid
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-355f89aa498a40cf9633c81fab3dfe52
Source dataset
uspto-grants-2016_05
Patent number
US09353096B2

Reaction notes

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