Sodium borohydride → HCID 59597440, compound

HRID 218639Notes

Reaction equation

HRID 218639 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]([C:25]2[CH:30]=[CH:29][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:27][CH:26]=2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:5][CH:4]=1)=[O:2].[BH4-].[Na+]>C(O)C.O1CCCC1>[OH:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][N:10]([C:25]2[CH:26]=[CH:27][C:28]([CH:31]([CH3:33])[CH3:32])=[CH:29][CH:30]=2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59597225HCID 59597225, compound

Product 1

HCID 59597440HCID 59597440, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

N-[(4-Formylphenyl)methyl]-N-(4-isopropylphenyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.42 g) was dissolved in a mixed solvent (10 mL) of ethanol: tetrahydrofuran (2:1), and sodium borohydride (0.15 g) was added under ice-cooling. The mixture was stirred at room temperature for 3 hr. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography to give N-{[4-(hydroxymethyl)phenyl]methyl}-N-(4-isopropylphenyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.25 g). melting point: 143.2° C.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-efd9bff5ce49414393f056701dd8d8ce
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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