Sodium borohydride → Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-(hydroxymethyl)-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

HRID 217529

Reaction equation

HRID 217529 reaction equation
[BH4-].[Na+].[F:3][C:4]([F:43])([F:42])[C:5]1[CH:6]=[C:7]([CH:35]=[C:36]([C:38]([F:41])([F:40])[F:39])[CH:37]=1)[CH2:8][N:9]([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]1[CH:30]=[C:29]([CH:31]=[O:32])[CH:28]=[CH:27][C:26]=1[O:33][CH3:34])[C:10](=[O:13])[O:11][CH3:12]>CO>[F:3][C:4]([F:42])([F:43])[C:5]1[CH:6]=[C:7]([CH:35]=[C:36]([C:38]([F:40])([F:39])[F:41])[CH:37]=1)[CH2:8][N:9]([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]1[CH:30]=[C:29]([CH2:31][OH:32])[CH:28]=[CH:27][C:26]=1[O:33][CH3:34])[C:10](=[O:13])[O:11][CH3:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11699919Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-formyl-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

Product 1

HCID 11585167Methyl [3,5-bis(trifluoromethyl)benzyl]{[5'-(hydroxymethyl)-2'-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (9.9 mg, 0.262 mmol) was added to a solution of methyl [3,5-bis(trifluoromethyl)benzyl]{[5′-formyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate (Example 73, 78 mg, 0.131 mmol) in methanol at room temperature. The reaction was stirred for one hour, then solvent was removed in vacuo. The title compound was obtained by column chromatography using 3:7 acetone/hexane. 1H NMR (CDCl3, 500 MHz) δ 7.25 (s, 1H), 7.30-7.62 (m, 6H), 7.08 (m, 1H), 6.94 (m, 1H), 4.64 (s, 2H), 4.15-4.40 (m, 4H), 3.64-3.74 (m, 6H). LC-MS (M-17) 578.0 (4.09 min).

Workup

  1. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-b70b6b2b66494c6eac409f46857c2c4e
Source dataset
uspto-grants-2012_06
Patent number
US08193365B2

Linked notes

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