Sodium borohydride → HCID 23599483, compound

HRID 1726356Notes

Reaction equation

HRID 1726356 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([NH:9][C:10]([C:12]1[S:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]=[O:24])[CH:18]=3)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2.[BH4-].[Na+]>CO>[N:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@@H:3]([NH:9][C:10]([C:12]1[S:13][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([CH2:23][OH:24])[CH:18]=3)=[CH:15][CH:16]=1)=[O:11])[CH2:2]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23599482HCID 23599482, compound

Product 1

HCID 23599483HCID 23599483, compoundYield 62.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of (R)-N-(1-azabicyclo[2.2.2]oct-3-yl)(5-(3-formylphenyl)thiophene-2-carboxamide) (875 mg) in methanol (15 mL), sodium borohydride (97.2 mg) was added. The mixture was then stirred at room temperature for 4 h. The residue was partitioned between water and chloroform. The extracts were dried over magnesium sulfate, filtered, and evaporated, and the residue was then purified by flash chromatography using 5-20% 3.5M methanolic ammonia/chloroform mixtures as the eluent to give the title compound (547 mg); MS (ES+) 343 (MH+).

Workup

  1. customThe residue was partitioned between water and chloroform
  2. dry with materialThe extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customthe residue was then purified by flash chromatography

Sources & evidence

ORD record
ord-4ca670eda5e344baad40061c13ef0a99
Source dataset
uspto-grants-2009_02
Patent number
US07491734B2

Reaction notes

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