Sodium borohydride → HCID 20766002, compound

HRID 984127Notes

Reaction equation

HRID 984127 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5](=[O:20])[CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([S:17]C#N)=[CH:14][CH:15]=2)[CH2:10][CH2:9]1>CO>[CH3:3][O:4][C:5](=[O:20])[CH2:6][CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([SH:17])=[CH:14][CH:15]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20766003HCID 20766003, compound

Product 1

HCID 20766002HCID 20766002, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.6 g) was added to a solution of compound 21B (0.65 g) in 20 mL of MeOH at 0° C. by portion in 15 minutes period. The mixture was stirred for another 30 minutes at RT, quenched with 50 mL of water and 50 mL of ether. The organic layer was separated, washed with water, brine, dried (MgSO4), concentrated to afford compound 21C (0.42 g). MS: 236 (M−1)+. Preparation of 3-{5-[4-Methyl-2-(4-trifluoromethyl-pheny)-thiazol-5-ylmethylsulfanyl]-2,3-dihydro-indol-1-yl}-propionic acid methyl ester (Compound 21D)

Workup

  1. customquenched with 50 mL of water and 50 mL of ether
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fea05bf60bc74035acf93be1514d89e7
Source dataset
uspto-grants-2005_03
Patent number
US06867224B2

Reaction notes

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