Hydrochloric Acid → (S)-1-Cbz-3-Aminopyrrolidine

HRID 1669996Notes

Reaction equation

HRID 1669996 reaction equation
[C:1]([N:11]1[CH2:15][CH2:14][C@H:13]([NH:16]C(OC(C)(C)C)=O)[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl>CCOC(C)=O>[C:1]([N:11]1[CH2:15][CH2:14][C@H:13]([NH2:16])[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14555479Benzyl (3S)-3-[(tert-butoxycarbonyl)amino]pyrrolidine-1-carboxylate2×

Product 1

HCID 1519355(S)-1-Cbz-3-AminopyrrolidineYield 98.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

The product of Step A, (3S)-1-Cbz-3-(N-BOC-amino)pyrrolidine, (5.26 g, 16.4 mmol) was dissolved in EtOAc (50 mL) and treated with a saturated HCl in EtOAc (15 mL). After the reaction mixture was stirred at rt for 30 min., the volatiles were removed to provide the title compound (4.11 g, 98.1%) as a colorless solid. The crude product was used without further purification.

Workup

  1. customthe volatiles were removed

Sources & evidence

ORD record
ord-1af6f58688b54344abfdf0b48db895cb
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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