Triphenylphosphine → HCID 54275154, compound

HRID 975640Notes

Reaction equation

HRID 975640 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][CH2:14][CH2:15][N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1)=[O:6])[CH:2]=[CH2:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[C:52]([OH:60])(=[S:59])[C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1>O1CCCC1.C(OCC)(=O)C>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@@H:10]([S:59][C:52](=[O:60])[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH2:9][C@H:8]1[CH2:13][CH2:14][CH2:15][N:16]1[CH:20]=[CH:19][N:18]=[CH:17]1)=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53832192HCID 53832192, compoundHCID 178526132HCID 178526132, compound

Product 1

HCID 54275154HCID 54275154, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2R,4R)-1-allyloxycarbonyl-4-hydroxy-2-[3-(imidazol-1-yl)propyl]pyrrolidine (12.5 g) in tetrahydrofuran (125 ml) were added successively triphenylphosphine (17.6 g) and diethyl azodicarboxylate (10.6 ml) at -10° C. and the solution was stirred at the same temperature for 30 minutes. Then thiobenzoic acid (9.5 ml) was added at the same temperature and the solution was stirred for 3 hours. To the solution was added ethyl acetate (125 ml) and washed with saturated aqueous sodium hydrogen carbonate (125 ml×2) and brine (250 ml). The solution was dried over magnesium sulfate and the solvent was evaporated to give a yellow oil. The oil was chromatographed on a 500 g of silica gel to give (2R,4S)-1-allyloxycarbonyl-4-benzoylthio-2-[3-(imidazol-1-yl)propyl]pyrrolidine (15.3 g) as a yellow paste.

Workup

  1. stirringthe solution was stirred for 3 hours
  2. washwashed with saturated aqueous sodium hydrogen carbonate (125 ml×2) and brine (250 ml)
  3. dry with materialThe solution was dried over magnesium sulfate
  4. customthe solvent was evaporated
  5. customto give a yellow oil
  6. customThe oil was chromatographed on a 500 g of silica gel

Sources & evidence

ORD record
ord-a959da8058d74f169a773da0791f1ac4
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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