Hydrochloric Acid → tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

HRID 2306261Notes

Reaction equation

HRID 2306261 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([NH:13]C(=O)C(F)(F)F)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>C1COCC1>[NH2:13][C@H:10]1[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 18725671HCID 18725671, compound

Product 1

HCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (S)-1-(tert-butoxycarbonyl)-3-(trifluoro-acetamido)pyrrolidine, as described above in Step A, (2.80 g, 9.5 mmol) in THF (80 mL) and H2O (10 mL) was added 1.0 N aqueous lithium hydroxide (10.5 mL, 10.5 mmol) and the resulting mixture was stirred at ambient temperature for 18 hours, then adjusted to pH 7 with 1.0 N aqueous HCl and concentrated to dryness in vacuo to give the titled compound.

Workup

  1. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-3cdf328af222441b81346a6874d86d66
Source dataset
uspto-grants-2002_08
Patent number
US06441017B1

Reaction notes

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