Hydrochloric Acid → 4-Nitrobenzyl (2S,4S)-4-(Acetylthio)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 1088265Notes

Reaction equation

HRID 1088265 reaction equation
[N+:1]([C:4]1[CH:31]=[CH:30][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18](=[O:20])[CH3:19])[CH2:14][C@H:13]2[CH2:21][O:22][Si](C(C)(C)C)(C)C)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl>CO.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18](=[O:20])[CH3:19])[CH2:14][C@H:13]2[CH2:21][OH:22])=[O:11])=[CH:30][CH:31]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 15671473(2S,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-t-butyldimethylsilyloxymethyl-4-acetylthiopyrrolidine

Product 1

HCID 102695344-Nitrobenzyl (2S,4S)-4-(Acetylthio)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

(2S,4S)-1-(p-Nitrobenzyloxycarbonyl)-2-t-butyldimethylsilyloxymethyl-4-acetylthiopyrrolidine (0.85 g) was dissolved in methanol (8.5 ml), and 0.85 ml of 6N hydrochloric acid was added thereto. The resulting mixture was stirred at room temperature for 2.5 hours, diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate and distilled to remove the solvent. Recrystallization of the residue from diethyl ether gave (2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-hydroxymethyl-4-acetylthiopyrrolidine.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. distillationdistilled
  4. customto remove the solvent
  5. customRecrystallization of the residue from diethyl ether

Sources & evidence

ORD record
ord-aebcf3f3458a426fbfad4b8ed37c3346
Source dataset
uspto-grants-1990_10
Patent number
US04962103

Reaction notes

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