Triphenylphosphine → HCID 57063518, compound

HRID 975664Notes

Reaction equation

HRID 975664 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10](O)[CH2:9][C@H:8]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[O:6])[CH:2]=[CH2:3].[C:20]([OH:28])(=[S:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.O.C(OCC)(=O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:27][C:20](=[O:28])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:9][C@H:8]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)=[O:6])[CH:2]=[CH2:3]

Participants

8

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 54160796HCID 54160796, compoundHCID 178526132HCID 178526132, compound

Product 1

HCID 57063518HCID 57063518, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-(2-pyridylmethyl) pyrrolidine (1.0 g), thiobenzoic acid (973 μl) and triphenylphosphine (1.30 g) in tetrahydrofuran (20 ml) was added dropwise diethyl azodicarboxylate (1.2 ml) at 0° C. The reaction mixture was stirred for 30 minutes, and then diluted with water and ethyl acetate. The aqueous layer was separated and extracted twice with ethyl acetate. The combined organic layer was washed with water (twice) and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was column chromatographed on silica gel to give (2R,4S)-1-allyloxycarbonyl-4-benzoylthio-2-(2-pyridylmethyl)pyrrolidine (1.34 g).

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted twice with ethyl acetate
  3. washThe combined organic layer was washed with water (twice) and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-ebdf79679a9347029a111b60e99189d6
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

Loading…