Hydrochloric Acid → HCID 86745516, compound

HRID 2371409Notes

Reaction equation

HRID 2371409 reaction equation
[CH3:1][N:2]1[CH2:6][C@@H:5]([S:7]C(=O)C)[CH2:4][C@H:3]1[CH2:11][O:12]C(=O)C.C[O-].[Na+].[ClH:19]>CO>[ClH:19].[CH3:1][N:2]1[CH2:6][C@@H:5]([SH:7])[CH2:4][C@H:3]1[CH2:11][OH:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 56631264HCID 56631264, compound

Product 1

HCID 86745516HCID 86745516, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (2S,4S)-1-methyl-2-acetoxymethyl-4-acetylthiopyrrolidine (231 mg) in methanol (2.4 ml), a solution of sodium methoxide (130 mg) in methanol (1.4 ml) was added at room temperature under nitrogen stream, and the resultant mixture was stirred at the same temperature for 19 minutes. The reaction mixture was combined with conc. hydrochloric acid (375 mg), followed by removal of the solvent. The residue was dissolved in a mixture of chloroform and methanol (4:1) and dried over magnesium sulfate. Removal of the solvent gave (2S,4S)-1-methyl-2-hydroxymethyl-4-mercaptopyrrolidine hydrochloride.

Workup

  1. customfollowed by removal of the solvent
  2. dissolutionThe residue was dissolved in a mixture of chloroform and methanol (4:1)
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-f7f090d1eec34a3290844ecaa48edbd2
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

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