Sodium borohydride → HCID 4279899, compound

HRID 397032Notes

Reaction equation

HRID 397032 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][C:23]([O:27][CH3:28])=[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:12]=[CH:13][C:14]([CH:17]2[C:26]3[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=3)[CH2:20][CH2:19][NH:18]2)=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18172438HCID 18172438, compound

Product 1

HCID 4279899HCID 4279899, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (10.874 g, 287.3 mmol) was added in small portions to a solution of 1-(4-benzyloxyphenyl)-6-methoxy-3,4-dihydroisoquinoline (54.56 g, 143.6 mmol) in MeOH (600 ml) at 0° C. The reaction mixture was stirred at 0° C. for 1 hr, then quenched by the dropwise addition of H2O (20 ml). The resulting mixture was concentrated in vacuo to a volume of about 100 ml. The solid that separated was collected to give 35.926 g (72% yield) of white solid.

Workup

  1. customquenched by the dropwise addition of H2O (20 ml)
  2. concentrationThe resulting mixture was concentrated in vacuo to a volume of about 100 ml
  3. customThe solid that separated
  4. customwas collected

Sources & evidence

ORD record
ord-f056c0e4cb44435f87745be404c60ca2
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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