Sodium borohydride → HCID 18172410, compound

HRID 397038Notes

Reaction equation

HRID 397038 reaction equation
[BH4-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][N:18]=2)=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][NH:18]2)=[CH:13][CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18172446HCID 18172446, compound

Product 1

HCID 18172410HCID 18172410, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (0.34 g, 0.89 mmol) was added in small portions to a solution of 1-(4-benzyloxyphenyl)-3,4-dihydroisoquinoline (0.139 g, 0.44 mmol) in MeOH (10 ml) at 0° C. The reaction mixture was stirred at 0° C. for 30 min, stirred at rt for 1 hr, then quenched by the dropwise addition of H2O (1.0 ml). The resulting mixture was concentrated in vacuo to remove the methanol, and the remaining aqueous layer was extracted with CHCl3 (4×10 ml). The combined extracts were dried over MgSO4 and concentrated in vacuo to give 0.138 g (99% yield) of colorless oil.

Workup

  1. stirringstirred at rt for 1 hr
  2. customquenched by the dropwise addition of H2O (1.0 ml)
  3. concentrationThe resulting mixture was concentrated in vacuo
  4. customto remove the methanol
  5. extractionthe remaining aqueous layer was extracted with CHCl3 (4×10 ml)
  6. dry with materialThe combined extracts were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74bfd9601ac04e8c89d128cfd1fcc695
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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