Triphenylphosphine → (2S,4S)-1-methyl-2-aminocarbonyl-4-acetylthiopyrrolidine

HRID 2371393Notes

Reaction equation

HRID 2371393 reaction equation
[CH3:1][N:2]1[CH2:6][C@H:5](O)[CH2:4][C@H:3]1[C:8]([NH2:10])=[O:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:42]([OH:45])(=[S:44])[CH3:43]>CN(C)C=O.ClCCl>[CH3:1][N:2]1[CH2:6][C@@H:5]([S:44][C:42](=[O:45])[CH3:43])[CH2:4][C@H:3]1[C:8]([NH2:10])=[O:9]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 10920632(2S,4R)-4-Hydroxy-1-methylpyrrolidine-2-carboxamideHCID 178418634HCID 178418634, compound

Product 1

HCID 56626958(2S,4S)-1-methyl-2-aminocarbonyl-4-acetylthiopyrrolidine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

(2S,4R)-1-Methyl-2-aminocarbonyl-4-hydroxypyrrolidine (540 mg) was dissolved in dry dimethylformamide (10 ml), and triphenylphosphine (1.78 g) was added thereto. To the resultant mixture, diethyl azodicarboxylate (1.07 ml) was added under nitrogen steam while ice-cooling, and the mixture was stirred for 35 minutes. Thioacetic acid (0.76 ml) was added to the mixture under ice-cooling, and stirring was continued for 30 minutes under ice-cooling and at room temperature for 4 hours. The reaction mixture was diluted with dichloromethane, washed with aqueous sodium bicarbonate solution and dried over magnesium sulfate. After removal of the solvent, the residue was purified by silica gel column chromatography to give (2S,4S)-1-methyl-2-aminocarbonyl-4-acetylthiopyrrolidine.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirring
  4. waitwas continued for 30 minutes under ice-
  5. washwashed with aqueous sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. customAfter removal of the solvent
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-917ff102df054d88b194bdc8918e6ac5
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

Loading…