Acetone → HCID 68767705, compound

HRID 1455474Notes

Reaction equation

HRID 1455474 reaction equation
[CH:1]([S:4]([CH2:7][C@H:8]1[C@@H:13]([N:14]2[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:15]2=[O:32])[CH2:12][CH2:11][NH:10][CH2:9]1)(=[O:6])=[O:5])([CH3:3])[CH3:2].[CH3:33][C:34]([CH3:36])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:34]([N:10]1[CH2:11][CH2:12][C@H:13]([N:14]2[CH2:18][CH2:17][C@H:16]([NH:19][C:20](=[O:31])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:29])([F:28])[F:30])[CH:22]=3)[C:15]2=[O:32])[C@H:8]([CH2:7][S:4]([CH:1]([CH3:3])[CH3:2])(=[O:5])=[O:6])[CH2:9]1)([CH3:36])[CH3:33]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 68771453HCID 68771453, compound

Product 1

HCID 68767705HCID 68767705, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A sample of N-((S)-1-((3R,4S)-3-(isopropylsulfonylmethyl)piperidin-4-yl)-2-oxopyrrolidin-3-yl)-3-(trifluoromethyl)benzamide (0.05 g) was dissolved in 1,2-dichloroethane (3 mL) prior to the addition of acetone (0.38 mL, 0.525 mMol). After stirring at rt for 1 h, sodium triacetoxyborohydride (0.445 g, 0.21 mMol) was added to the reaction. Stirring was continued for 2 h when the reaction was quenched with saturated NaHCO3. Partitioned between EtOAc and water. Organic layer was washed with brine and dried (MgSO4). Filtered, concentrated and chromatographed. The desired product, N-((S)-1-((3R,4S)-1-isopropyl-3-(isopropylsulfonylmethyl)piperidin-4-yl)-2-oxopyrrolidin-3-yl)-3-(trifluoromethyl)benzamide (0.0086 g, yield=16%) was obtained as a white solid. MS found: (M+H)+=518.2

Workup

  1. stirringStirring
  2. waitwas continued for 2 h
  3. customwhen the reaction was quenched with saturated NaHCO3
  4. customPartitioned between EtOAc and water
  5. washOrganic layer was washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationFiltered
  8. concentrationconcentrated
  9. customchromatographed

Sources & evidence

ORD record
ord-9a11850a3fa44bc5a4362c584a770396
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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