Hydrochloric Acid → (2S)-5-allyloxycarbonylimino-2-hydroxymethyl-1-methylpyrrolidine

HRID 1090525Notes

Reaction equation

HRID 1090525 reaction equation
[CH2:1]([O:4][C:5]([N:7]=[C:8]1[N:12]([CH3:13])[C@H:11]([CH2:14][O:15][Si](C(C)(C)C)(C)C)[CH2:10][CH2:9]1)=[O:6])[CH:2]=[CH2:3].Cl.C(=O)(O)[O-].[Na+]>CO>[CH2:1]([O:4][C:5]([N:7]=[C:8]1[N:12]([CH3:13])[C@H:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)=[O:6])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 57032378(2S)-5-allyloxycarbonylimino-2-t-butyldimethylsilyloxymethyl-1-methylpyrrolidine

Product 1

HCID 57267024(2S)-5-allyloxycarbonylimino-2-hydroxymethyl-1-methylpyrrolidineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S)-5-allyloxycarbonylimino-2-t-butyldimethylsilyloxymethyl-1-methylpyrrolidine (1.0 g) in methanol (30 ml) was added conc. hydrochloric acid (1 ml) at 0° C. After stirring at ambient temperature for 12 hours, saturated aqueous sodium bicarbonate was added to the mixture and the solvent was evaporated. The residue was dissolved in ethyl acetate and washed in turn with water and brine. The dried solution was evaporated in vacuo to give (2S)-5-allyloxycarbonylimino-2-hydroxymethyl-1-methylpyrrolidine (0.65 g).

Workup

  1. customthe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed in turn with water and brine
  4. customThe dried solution was evaporated in vacuo

Sources & evidence

ORD record
ord-fe185569312f40e994d5c6ea55bd3ec8
Source dataset
uspto-grants-1992_01
Patent number
US05081237

Reaction notes

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