Triphenylphosphine → HCID 56609827, compound

HRID 2371387Notes

Reaction equation

HRID 2371387 reaction equation
[CH3:1][N:2]1[CH2:6][C@H:5](O)[CH2:4][C@H:3]1[C:8]([N:10]([CH3:12])[CH3:11])=[O:9].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:44]([OH:47])(=[S:46])[CH3:45]>O1CCCC1.ClCCl>[CH3:1][N:2]1[CH2:6][C@@H:5]([S:46][C:44](=[O:47])[CH3:45])[CH2:4][C@H:3]1[C:8]([N:10]([CH3:12])[CH3:11])=[O:9]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 45116063HCID 45116063, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 56609827HCID 56609827, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2S,4R)-1-Methyl-2-dimethylaminocarbonyl-4-hydroxypyrrolidine (970 mg) was dissolved in dry tetrahydrofuran (11.1 ml), and triphenylphosphine (2.66 g) was added thereto. To the resultant mixture, diethyl azodicarboxylate (1.60 ml) was added under nitrogen steam while ice-cooling, and the mixture was stirred for 30 minutes. Thioacetic acid (1.45 ml) was added to the mixture under ice-cooling, and stirring was continued for 40 minutes under ice-cooling, followed by allowing to stand overnight. The reaction mixture was diluted with dichloromethane, washed with aqueous potassium carbonate solution and dried over magnesium sulfate. After removal of the solvent by distillation, the residue was purified by silica gel column chromatography to give (2S,4S)-1-methyl-2-dimethylaminocarbonyl-4-acetylthiopyrrolidine.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringstirring
  4. waitwas continued for 40 minutes under ice-
  5. temperaturecooling
  6. waitto stand overnight
  7. washwashed with aqueous potassium carbonate solution
  8. dry with materialdried over magnesium sulfate
  9. customAfter removal of the solvent
  10. distillationby distillation
  11. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-acd768fa2c424d1c8e89b38b2b0efafe
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

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