Sodium borohydride → HCID 16005234, compound

HRID 1175613Notes

Reaction equation

[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:24])([CH3:23])[C:16]([NH:18][CH2:19][CH:20]([CH3:22])[CH3:21])=[O:17])=[CH:11][CH:10]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH3:23])([CH3:24])[C:16]([NH:18][CH2:19][CH:20]([CH3:21])[CH3:22])=[O:17])=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(2′-Formylbiphenyl-4-yl)-N-isobutyl-2-methylpropanamide (example 37) (190 mg, 0.59 mmol) was dissolved in anhydrous MeOH (6 mL) and the mixture was cooled to 0° C. A solution of NaBH4 (45 mg, 1.2 mmol) in anhydrous MeOH (4 mL) was then added to the solution. The mixture was stirred for 4 hrs at room temperature and then evaporated. The residue was dissolved in EtOAc and washed successively with water and brine, dried over MgSO4, filtered and evaporated. The residue was successively purified on preparative RP HPLC (acetonitrile/water) and on silica gel (EtOAc/hexanes) and co-evaporated with ethanol to give 119 mg (62%) of white crystals. 1H NMR (400 MHz, dMSO): δ 0.72-0.74 (d, 6H), 1.47 (s, 6H), 1.67-1.70 (m, 1H), 2.82-2.86 (t, 2H), 4.37-4.38 (d, 2H), 5.01-5.1 (t, 1H), 7.17 (d, 1H), 7.27-7.36 (m, 7H), 7.53-7.55 (d, 1H); MS+H (326).

Workup

customevaporated
dissolutionThe residue was dissolved in EtOAc
washwashed successively with water and brine
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customThe residue was successively purified on preparative RP HPLC (acetonitrile/water) and on silica gel (EtOAc/hexanes) and co-evaporated with ethanol

Sources & evidence

ORD record: ord-ea26167b372c423785f42f599275f8eb
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842324B2

Reaction notes

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