Sodium borohydride → 5-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl]thiophen-2-methanol

HRID 1921476Notes

Reaction equation

HRID 1921476 reaction equation
[CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([C:11]2[S:15][C:14]([CH:16]=[O:17])=[CH:13][CH:12]=2)[CH:4]=1)[CH3:2].[BH4-].[Na+]>CO>[CH2:1]([C:3]1[C:8](=[O:9])[NH:7][C:6]([CH3:10])=[C:5]([C:11]2[S:15][C:14]([CH2:16][OH:17])=[CH:13][CH:12]=2)[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 588085435-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl)thiophene-2-carbaldehyde

Product 1

HCID 588085615-(5-Ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl]thiophen-2-methanolYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(5-ethyl-2-methyl-6-oxo-1,6-dihydropyridin-3-yl]thiophen-2-carbaldehyde in methanol (5 mL/mmol) is added one molar equivalent of sodium borohydride at room temperature and the reaction mixture is stirred for about 6 hrs. at room temperature. The reaction mixture is then concentrated, taken up in dichloromethane and washed with water. The organic phase is concentrated and purified by RP-HPLC to give the title compound (20% yield) as a yellow solid. LC/MS: RT 1.90 min; m/e 250 (M+H); 1H NMR (δ, ppm): 11.66 (1H, br d), 7.25 (1H, s), 6.90 (2H, m), 5.45 (1H, t), 4.50 (2H, d), 2.38 (2H, q), 2.27 (3H, s), 1.11 (3H, t).

Workup

  1. customat room temperature
  2. concentrationThe reaction mixture is then concentrated
  3. washwashed with water
  4. concentrationThe organic phase is concentrated
  5. custompurified by RP-HPLC

Sources & evidence

ORD record
ord-495c58a7b01c4d1ab7d8bb9566520bb8
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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