Sodium borohydride → HCID 67070283, compound

HRID 2390851Notes

Reaction equation

HRID 2390851 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:5]([O:24][CH3:25])=[C:6]([CH2:8][C:9]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=2)([CH:11]=[O:12])[CH3:10])[CH:7]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:5]([O:24][CH3:25])=[C:6]([CH2:8][C:9]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])=[CH:15][CH:14]=2)([CH2:11][OH:12])[CH3:10])[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86638344HCID 86638344, compound

Product 1

HCID 67070283HCID 67070283, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

step 2—To a solution of 292 (117 mg, 0.243 mmol) in MeOH (5 mL) at 0° C. was added sodium borohydride (44 mg, 1.163 mmol). The solution was gradually warmed to RT over 3 h. The reaction was quenched with NH4Cl solution and extracted with EtOAc. The combined extracts were dried (Na2SO4), filtered and concentrated in vacuo to afford 111 mg of N-{4-[2-(5-bromo-3-tert-butyl-2-methoxy-phenyl)-1-hydroxymethyl-1-methyl-ethyl]-phenyl}-methanesulfonamide (294) a white foam (94%).

Workup

  1. customThe reaction was quenched with NH4Cl solution
  2. extractionextracted with EtOAc
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ddaff12a064f40d984d8348e3b145669
Source dataset
uspto-grants-2012_09
Patent number
US08273773B2

Reaction notes

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