Sodium Thiosulfate → 1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethan-1-one

HRID 344702Notes

Reaction equation

HRID 344702 reaction equation
[CH2:1]([N:8]([CH3:26])[C:9]([CH2:11][CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]([OH:25])[C:21]([F:24])([F:23])[F:22])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CCOCC.C(Cl)Cl>[CH2:1]([N:8]([CH3:26])[C:9]([CH2:11][CH2:12][C:13]([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 14995339(1RS)-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl) propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethanol

Product 1

HCID 156609871-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethan-1-oneYield 50.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of (1RS)-1-[(2S)-1-[3-(N-benzyl-N-methylcarbamoyl)propanoyl]pyrrolidin-2-yl]-2,2,2-trifluoroethanol (103 mg), Dess-Martin reagent (435 mg) and methylene chloride (1.5 ml) was stirred for 3 hrs. at room temperature. After reaction, the raction solution was diluted with ether. The diluted solution was added dropwise to a saturated aq. solution of sodium bicarbonate (30 ml) wherein sodium thiosulfate (3.0 g) was dissolved. The mixture was stirred for 10 mins at room temperature. The mixture was extracted with EtOAc. The extract was washed, dried and evaporated. The residue was purified by column chromatography on silica gel (hexane-EtOAc) to give the title compound (52 mg) having the following physical data:

Workup

  1. customat room temperature
  2. customAfter reaction
  3. dissolutionwas dissolved
  4. stirringThe mixture was stirred for 10 mins at room temperature
  5. extractionThe mixture was extracted with EtOAc
  6. washThe extract was washed
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel (hexane-EtOAc)

Sources & evidence

ORD record
ord-67f2e4b2fc494df28e31e3a2e8d59386
Source dataset
uspto-grants-1991_10
Patent number
US05053414

Reaction notes

Loading…