Sodium borohydride → HCID 22493824, compound

HRID 916876Notes

Reaction equation

HRID 916876 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-28d7f4a68bd84a378547de5e82153a4f
Source dataset
uspto-grants-2007_09
Patent number
US07271270B2

Reaction notes

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