Hydrochloric Acid → HCID 53794034, compound

HRID 620786Notes

Reaction equation

HRID 620786 reaction equation
C([Li])CCC.[CH2:6]([O:13][C:14]([N:16]1[CH2:20][C@H:19]([O:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][C@H:17]1[CH2:26][OH:27])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31].Cl>CCCCCC>[CH2:6]([O:13][C:14]([N:16]1[CH2:20][C@H:19]([O:21][S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][C@H:17]1[CH2:26][O:27][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 15117254Phenylmethyl (2S,4R)-2-(hydroxymethyl)-4-[(methylsulfonyl)oxy]-1-pyrrolidinecarboxylateHCID 178418339Butyllithium

Product 1

HCID 53794034HCID 53794034, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A 1.6M solution (4.2 ml) of butyllithium in hexane was added to a solution of (2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-methanesulfonyloxypyrrolidine (2.00 g) at -30°-20° C. with stirring in a stream of nitrogen and the mixture was stirred at the same temperature for 30 minutes. Ethyl bromoacetate (2.4 ml) was added to the mixture at -30°~-20° C. and the solution was stirred at 10-15° C. for 3 hours. The solution was poured into 0.1N hydrochloric acid (50 ml) extracted with ethyl acetate (50 ml), dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was subjected to a column chromatography on silica gel (20 g) and eluted with chloroform to give (2S,4R)-1-benzyloxycarbonyl-2-(ethoxycarbonylmethyl)oxymethyl-4-methanesulfonyloxypyrrolidine (1.87 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 30 minutes
  2. stirringthe solution was stirred at 10-15° C. for 3 hours
  3. extractionextracted with ethyl acetate (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto give a syrup
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-e57476425dbf4467957ce92d1953bb19
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

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