Sodium borohydride → HCID 58968618, compound

HRID 2075103Notes

Reaction equation

HRID 2075103 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](=[O:32])[CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1.[BH4-].[Na+]>CO>[F:39][C:36]([F:37])([F:38])[C:34]1[CH:33]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:40])[F:41])[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]([OH:32])[CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)[C:8]1[N:9]=[N:10][N:11]([CH3:13])[N:12]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58968639HCID 58968639, compound

Product 1

HCID 58968618HCID 58968618, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(2-(((3,5-bis(trifluoromethyl)benzyl)(2-methyl-2-H-tetrazol-5-yl)amino)methyl)-4-(trifluoromethyl)phenyl-2-cyclopentylethanone (123 mg, 0.207 mmol) in methanol (15 mL) was added sodium borohydride (7.8 mg, 0.207 mmol) at room temperature. After 1 hour the solvent was removed under reduced pressure, the residue dissolved in 20 mL of ethyl acetate (20 mL) and washed with water (10 mL). The combined organics were dried with anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The residue was dissolved in dichloromethane and purified by flash chromatography on a 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 0-60% ethyl acetate in heptane) to yield the title compound as a clear oil (0.025 gm). 1H NMR (400 MHz, CDCl3) δ 7.76 (s, 1H) 7.62 (s, 2H) 7.56(d, J=7.8 Hz, 1H) 7.34 (s, 1H) 4.96-4.92 (m, 1H) 4.85 (s, 2H) 4.81 (q, J=15.3 Hz, J=16.1 Hz, 2H) 4.2 (s, 3H) 1.9-1.4 (m, 11H).

Workup

  1. customAfter 1 hour the solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in 20 mL of ethyl acetate (20 mL)
  3. washwashed with water (10 mL)
  4. dry with materialThe combined organics were dried with anhydrous sodium sulfate
  5. concentrationconcentrated to dryness under reduced pressure
  6. dissolutionThe residue was dissolved in dichloromethane
  7. custompurified by flash chromatography on a 4 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 0-60% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-75016257beee4944b7d3768440be7e17
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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