Sodium borohydride → HCID 22493824, compound

HRID 1816413Notes

Reaction equation

HRID 1816413 reaction equation
[CH2:1]([N:5]1[C:9]([CH:10]=[O:11])=[CH:8][N:7]=[C:6]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+]>CO.O>[CH2:1]([N:5]1[C:9]([CH2:10][OH:11])=[CH:8][N:7]=[C:6]1[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 10633115HCID 10633115, compound

Product 1

HCID 22493824HCID 22493824, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Aldehyde 102 is dissolved in methanol (150 mL). Sodium borohydride (3 g) is added in portions. After the addition was complete, the reaction is diluted with water and concentrated. The residue is dissolved in ethyl acetate, washed with brine, dried (Na2SO4) and concentrated. The product is purified by flash chromatography on silica gel (5% MeOH/CHCl3) to give 4.17 g of 103 as a cream colored solid. 1H-NMR (400 MHz, CDCl3): δ 0.79 (3H, t, d=7.4), 1.18 (2H, m, d=7.4), 1.60 (2H, m, d=7.6), 4.03 (2H, dd, d=7.6), 4.56 (2H, s), 6.84 (1H, s), 7.39-7.50 (3H, m), 7.50-7.53 (2H, m).

Workup

  1. additionAfter the addition
  2. concentrationconcentrated
  3. dissolutionThe residue is dissolved in ethyl acetate
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe product is purified by flash chromatography on silica gel (5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-b2a867029e994f319cb9246566aea60e
Source dataset
uspto-grants-2005_04
Patent number
US06884815B1

Reaction notes

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