Acetic Acid → N-(4-Chlorobenzyl)-2-(hydroxymethyl)-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

HRID 23641Notes

Reaction equation

HRID 23641 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:30])[C:12]3[S:19][C:18]([CH:20]=[O:21])=[C:17]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:4][CH:3]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[C:11](=[O:30])[C:12]3[S:19][C:18]([CH2:20][OH:21])=[C:17]([CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:27])([CH3:28])[CH3:29])[C:13]=3[N:14]([CH3:16])[CH:15]=2)=[O:9])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 22574364N-(4-Chlorobenzyl)-2-formyl-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide

Product 1

HCID 22574330N-(4-Chlorobenzyl)-2-(hydroxymethyl)-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamideYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (0° C.), stirred solution of 1.56 g of N-(4-chlorobenzyl)-2-formyl-4-methyl-7-oxo-3-{[2-(trimethylsilyl)ethoxy]methyl}-4,7-dihydrothieno[3,2-b]pyridine-6-carboxamide And 0.91 mL of acetic acid in 32 mL of CH2Cl2 is added 1.7 g of sodium triacetoxyborohydride. The ice bath is removed and the reaction allowed to stir at room temperature for 4 h, then partitioned between chloroform and aq. NaHCO3. The organic phase is dried (Na2SO4) and concentrated under reduced pressure, and the residue flash chromatographed on silica using 2% MeOH in CH2Cl2 to provide 1.53 g of the title compound as a pale yellow solid. Recrystallization from acetonitrile furnishes white platelets.

Workup

  1. customThe ice bath is removed
  2. custompartitioned between chloroform and aq. NaHCO3
  3. dry with materialThe organic phase is dried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customthe residue flash chromatographed on silica using 2% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-f8ec37a6573e49e3bd07a2ee93ebdeb3
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

Loading…