Sodium borohydride → HCID 22493824, compound

HRID 1643180Notes

Reaction equation

HRID 1643180 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 (3g) is added in portions. After the addition is 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 103 as a cream colored solid. 1HNMR (400 MHz, CDCl3) δ 0.79 (3H, t, J=7.4 Hz), 1.18 (2H, m, J=7.4 Hz), 1.60 (2H, m, J=7.6 Hz), 4.03 (2H, dd, J=7.6 Hz), 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-de3defc27b504d9a9e248f71b8c08870
Source dataset
uspto-grants-2012_02
Patent number
US08119665B2

Reaction notes

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