Hydrochloric Acid → Ethyl L-prolinate hydrochloride

HRID 333317Notes

Reaction equation

HRID 333317 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([O:8][CH2:9][CH3:10])=[O:7].[ClH:18].O1CCOCC1>>[ClH:18].[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 10857688HCID 10857688, compound

Product 1

HCID 11679912Ethyl L-prolinate hydrochloride

Procedure

A mixture of (S)-1-tert-butyl 2-ethyl pyrrolidine-1,2-dicarboxylate (200 mg, 0.822 mmol) and HCl in 1,4-dioxane (4110 μl, 16.44 mmol) was allowed to stir for 1 hour. The reaction mixture was concentrated to give (S)-ethyl pyrrolidine-2-carboxylate hydrochloride; 1H NMR (400 MHz, CDCl3) δ ppm 1.32 (t, J=7.2 Hz, 3H) 2.00-2.22 (m, 3H) 2.39-2.48 (m, 1H) 3.49-3.67 (m, 2H) 4.29 (q, J=7.2 Hz, 3H) 9.09 (br s, 1H) 10.98 (br s, 1H).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-bc39dfabe43f419e8bd92199ea938bcb
Source dataset
uspto-grants-2014_11
Patent number
US08877815B2

Reaction notes

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