Sodium borohydride → (2-{[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclohexyl-methanol

HRID 2075081Notes

Reaction equation

HRID 2075081 reaction equation
[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:35]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[C:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)=[O:26])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[BH4-].[Na+]>CO>[F:41][C:2]([F:1])([F:40])[C:3]1[CH:4]=[C:5]([CH:33]=[C:34]([C:36]([F:37])([F:38])[F:39])[CH:35]=1)[CH2:6][N:7]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=1[CH:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[OH:26])[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58968633(2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclohexyl-methanone

Product 1

HCID 58968665(2-{[(3,5-Bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclohexyl-methanolYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (2-{[(3,5-bis-trifluoromethyl-benzyl)-(2-methyl-2H-tetrazol-5-yl)-amino]-methyl}-4-trifluoromethyl-phenyl)-cyclohexyl-methanone (152 mg; 0.256 mmol) and sodium borohydride (22 mg; 0.582 mmol) in methanol (1.5 mL) was stirred at room temperature for 16 hours. The solvent was evaporated under reduced pressure. The residue was taken up in ethyl acetate, washed twice with water and then brine. The organic layer was dried sodium sulfate and concentrated under reduced pressure. The residue was purified over 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 20-50% ethyl acetate in heptane) to give 152 mg (99.7% yield) of the title compound as a colorless gum. MS (ES+): Calc: 595.5, Found: 596.1 (M+H). 1H NMR (400 MHz, CDCl3) δ ppm 7.78 (s, 1H), 7.66 (s, 2H), 7.57 (d, J=8.30 Hz, 1H), 7.55 (d, J=8.30 Hz, 1H), 7.36 (s, 1H), 4.88 (d, J=15.77 Hz, 1H), 4.79 (d, J=15.77 Hz, 1H), 4.76 (d, J=15.77 Hz, 1H), 4.70 (d, J=16.18 Hz, 1H), 4.66 (d, J=7.05 Hz, 1H), 4.21 (s, 3H), 2.20 (bs, 1H), 1.94 (d, J=12.45 Hz, 1H), 1.78 (m, 1H), 1.69-1.51 (m, 4H), 1.2-0.88 (m, 4H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washwashed twice with water
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified over 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 20-50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-54967d4a3d5e48ceb936e73c3bf3c703
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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