Sodium borohydride → HCID 18172397, compound

HRID 397045Notes

Reaction equation

HRID 397045 reaction equation
[BH4-].[Na+].[CH:3]1([C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH2:12][CH2:11][N:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>CO>[CH:3]1([CH:9]2[C:18]3[C:13](=[CH:14][C:15]([O:19][CH3:20])=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18172454HCID 18172454, compound

Product 1

HCID 18172397HCID 18172397, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (0.512 g, 13.5 mmol) was added in small portions to a solution of 1-cyclohexyl-6-methoxy-3,4-dihydroisoquinoline (0.822 g, 3.38 mmol) in MeOH (40 ml) at 0° C. The reaction mixture was stirred at 0° C. for 30 min, warmed to rt and stirred at rt for 15 hr, then quenched by the dropwise addition of H2O (5.0 ml). The resulting mixture was concentrated in vacuo to remove the MeOH and the remaining aqueous solution was extracted with CHCl3 (4×10 ml). The combined extracts were dried over MgSO4 and concentrated in vacuo to give 0.775 g (93% yield) of yellow oil.

Workup

  1. temperaturewarmed to rt
  2. stirringstirred at rt for 15 hr
  3. customquenched by the dropwise addition of H2O (5.0 ml)
  4. concentrationThe resulting mixture was concentrated in vacuo
  5. customto remove the MeOH
  6. extractionthe remaining aqueous solution was extracted with CHCl3 (4×10 ml)
  7. dry with materialThe combined extracts were dried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-acb3efe5a6e94145ab4eb842b83928a6
Source dataset
uspto-grants-2003_08
Patent number
US06608203B2

Reaction notes

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