tert-Butyl (S)-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-carbonyl)pyrrolidine-1-carboxylate → (S)-1-Boc-2-(3-ethoxy-3-oxopropanoyl)pyrrolidine

HRID 458404Notes

Reaction equation

HRID 458404 reaction equation
[CH3:1][C:2]1(C)OC(=O)[CH:5]([C:9]([C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:10])[C:4](=[O:23])[O:3]1>CCO>[CH2:2]([O:3][C:4](=[O:23])[CH2:5][C:9]([C@@H:11]1[CH2:15][CH2:14][CH2:13][N:12]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[O:10])[CH3:1]

Participants

3

Reactant 1

HCID 67415065tert-Butyl (S)-2-(2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-carbonyl)pyrrolidine-1-carboxylate

Product 1

HCID 57407385(S)-1-Boc-2-(3-ethoxy-3-oxopropanoyl)pyrrolidineYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

tert-Butyl (2S)-2-[(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)carbonyl]-1-pyrrolidinecarboxylate (85 g, 250 mmol) was dissolved in 500 mL absolute EtOH and refluxed for 3 h. Concentration provided the title compound as a light yellow oil (68.4 g, 240 mmol, 96%). 1H NMR (400 MHz, CDCl3, mixture of rotamers and keto/enol tautomers) δ 4.35 (m, 0.5H), 4.25 (m, 0.5H), 4.17 (m, 2H), 3.6–3.4 (m, 3H), 2.2–1.8 (m, 4H), 1.4 (m, 9H), 1.15 (m, 3H) ppm.

Workup

  1. temperaturerefluxed for 3 h
  2. concentrationConcentration

Sources & evidence

ORD record
ord-4363fe97e81e4973bec9f1f23beb1a44
Source dataset
uspto-grants-2007_03
Patent number
US07189851B2

Reaction notes

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