Sodium borohydride → HCID 3954509, compound

HRID 397042Notes

Reaction equation

HRID 397042 reaction equation
[BH4-].[Na+].Cl.[I:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13][N:12]=2)=[CH:7][CH:6]=1>CO>[I:4][C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13][NH:12]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18172383HCID 18172383, compound

Product 1

HCID 3954509HCID 3954509, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (2 g, 52.9 mmol) was added in small portions to a solution of 1-(4-iodophenyl)-6-methoxy-3,4-dihydroisoquinoline hydrochloride (7.5 g, 18.7 mmol) in MeOH (100 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 remove most of the MeOH, then EtOAc was added. The resulting mixture was extracted with 1M NaOH (2×25 ml), then saturated NaCl solution (25 ml), dried over MgSO4, and evaporated in vacuo to give 6.2 g (65% yield) of white solid.

Workup

  1. customquenched by the dropwise addition of H2O (20 ml)
  2. concentrationThe resulting mixture was concentrated in vacuo
  3. customto remove most of the MeOH
  4. additionEtOAc was added
  5. extractionThe resulting mixture was extracted with 1M NaOH (2×25 ml)
  6. dry with materialsaturated NaCl solution (25 ml), dried over MgSO4
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-39e07f20541b4f4683a079b62ddc1074
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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