Methanol → HCID 66616515, compound

HRID 1889719Notes

Reaction equation

HRID 1889719 reaction equation
[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][CH2:7][NH:8][C:9](=O)[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][S:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:11]=2)=[CH:4][CH:3]=1.B.C1COCC1.CO.C(O)(C(F)(F)F)=O>C1COCC1>[F:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][CH2:7][NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][S:17][CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:11]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 2723981Borane;tetrahydrofuranHCID 66616681HCID 66616681, compound

Product 1

HCID 66616515HCID 66616515, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(4-fluorophenethyl)-3-(phenethylthiomethyl)benzamide (0.3 g, 0.76 mmol) in THF (5 mL) was added borane-THF complex (1 M solution in THF, 12 mL, 12 mmol). The reaction mixture was stirred at rt for overnight. To the reaction mixture was added MeOH and 2 mL of TFA, and the resulting mixture was stirred for 3 h. The resulting mixture was concentrated and the residue was diluted with saturated NaHCO3 solution and ethyl acetate. The organic layer was separated, washed with brine, and dried over MgSO4. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography silica gel eluting with 20% ethyl acetate in hexanes, which contained 10% of 2 M ammonia in MeOH to give the desired product (0.18 g, 58%) as a colorless oil. 1H NMR (CDCl3) δ 7.32-7.14 (m, 11H), 7.01-6.95 (m, 2H), 3.84 (s, 2H), 3.72 (s, 2H), 2.91-2.80 (m, 6H), 2.73-2.64 (m, 2H). MS (ESI): 380.1 (M+H)+.

Workup

  1. stirringthe resulting mixture was stirred for 3 h
  2. concentrationThe resulting mixture was concentrated
  3. additionthe residue was diluted with saturated NaHCO3 solution and ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was purified by flash chromatography silica gel eluting with 20% ethyl acetate in hexanes, which

Sources & evidence

ORD record
ord-44bbb77f238d4e7f9171e644279eac0c
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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