Sodium borohydride → HCID 59438437, compound

HRID 2177544Notes

Reaction equation

HRID 2177544 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([S:30][CH3:31])[C:4]=1[C:5]([NH:7][C:8]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13][C:12](=[O:14])[CH2:11][N:10]([CH3:15])[CH2:9]1)=[O:6].[BH4-].[Na+]>CO>[OH:14][CH:12]1[CH2:11][N:10]([CH3:15])[CH2:9][C:8]([NH:7][C:5](=[O:6])[C:4]2[C:22]([S:30][CH3:31])=[CH:23][C:24]([C:26]([F:27])([F:28])[F:29])=[CH:25][C:3]=2[O:2][CH3:1])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59438442HCID 59438442, compound

Product 1

HCID 59438437HCID 59438437, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 23 mg (0.0508 mmol) rac-2-methoxy-N-(1-methyl-5-oxo-3-phenyl-piperidin-3-yl)-6-methylsulfanyl-4-trifluoromethyl-benzamide in 0.46 ml methanol was added 3.9 mg (0.102 mmol) sodium borohydride. The mixture was stirred at room temperature for 30 minutes, quenched with 1.0 ml HCl 1N and stirred for 15 minutes. Water was added and the mixture was basified with a 2M sodium carbonate solution. The mixture was extracted 3 times with dichloromethane. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on silica gel (Eluent: heptane/ethyl acetate 0 to 100%) to provide 4.5 mg (20%) of the title compound as a white solid. MS (m/e): 455.2 (MH+).

Workup

  1. customquenched with 1.0 ml HCl 1N
  2. stirringstirred for 15 minutes
  3. additionWater was added
  4. extractionThe mixture was extracted 3 times with dichloromethane
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified on silica gel (Eluent: heptane/ethyl acetate 0 to 100%)

Sources & evidence

ORD record
ord-fc7fd5e68d1c4852af61ae355aad0a80
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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