Hydrochloric Acid → (S)-tert-Butyl (1-amino-2-oxopyrrolidin-3-yl)carbamate

HRID 2086252Notes

Reaction equation

HRID 2086252 reaction equation
C(OC([NH:8][N:9]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]1=[O:22])=O)(C)(C)C.Cl>CO.C(OCC)(=O)C>[NH2:8][N:9]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[C:10]1=[O:22]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69545784(3S)-1,3-bis(tert-Butoxycarbonylamino)-2-pyrrolidone

Product 1

HCID 45092234(S)-tert-Butyl (1-amino-2-oxopyrrolidin-3-yl)carbamateYield 87.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3S)-1,3-bis(tert-butoxycarbonylamino)-2-pyrrolidone (3.15 g) in methanol (10 ml) was combined with a 4N solution of hydrochloric acid in ethyl acetate (20 ml) and stirred at room temperature for 30 minutes. The reaction mixture was concentrated, and the resultant residue was combined with dichloromethane (30 ml) and triethylamine (6.06 g), and then with di-tert-butyl dicarbonate (2.62 g) at 0° C. and stirred at room temperature for 1 hour. The reaction mixture was combined with an aqueous solution of sodium carbonate, extracted with dichloromethane, dried and concentrated. The residue obtained was washed with hexane to obtain (3S)-1-amino-3-(tert-butoxycarbonylamino)-2-pyrrolidone (1.89 g) as a colorless solid.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. stirringwith di-tert-butyl dicarbonate (2.62 g) at 0° C. and stirred at room temperature for 1 hour
  3. extractionextracted with dichloromethane
  4. customdried
  5. concentrationconcentrated
  6. customThe residue obtained
  7. washwas washed with hexane

Sources & evidence

ORD record
ord-2fc66122ab0a4aa6a7819cfc485fb82f
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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