Sodium borohydride → HCID 58554152, compound

HRID 2410499Notes

Reaction equation

HRID 2410499 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[CH3:15])=[C:6]([CH:9]=1)[CH:7]=[O:8].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:14][CH2:13][CH2:12][CH:11]2[CH3:15])=[C:6]([CH2:7][OH:8])[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23091110HCID 23091110, compound

Product 1

HCID 58554152HCID 58554152, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-bromo-2-(2-methylpyrrolidin-1-yl)benzaldehyde (17 g, 63.4 mmol) in methanol (150 mL) under nitrogen was added sodium borohydride (2.41 g, 63.4 mmol) at 0° C. in portions. The reaction mixture was stirred at RT for 1 hour, then evaporated to remove methanol. The resulting crude was taken up with water (250 mL) and extracted with EtOAc (150 mL). The organic layer was washed with water, then dried (Na2SO4) and concentrated under reduced pressure to afford the title compound as a yellow oil (16 g, 93%). 1H NMR (DMSO-d6, 400 MHz) δ 7.53 (1H, d), 7.27 (1H, d), 6.87 (1H, d), 5.22 (1H, t), 4.42 (2H, m), 3.56 (1H, m), 3.36 (1H, m), 2.70 (1H, m), 2.49 (1H, m) 2.09 (1H, m), 1.83 (1H, m), 1.73 (1H, m), 1.47 (1H, m), 0.90 (3H, d).

Workup

  1. customevaporated
  2. customto remove methanol
  3. extractionextracted with EtOAc (150 mL)
  4. washThe organic layer was washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7ce135a72c65417a9e733cea75e668ee
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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