Acetic Acid → (S)-2-(Acetoxyacetyl)-1-(tert-butoxycarbonyl)pyrrolidine

HRID 1735390Notes

Reaction equation

HRID 1735390 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13](=[O:17])[CH:14]=[N+]=[N-])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:18]([OH:21])(=[O:20])[CH3:19]>>[C:18]([O:21][CH2:14][C:13]([C@@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:17])(=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 53788513(S)-tert-Butyl 2-(2-diazoacetyl)pyrrolidine-1-carboxylate

Product 1

HCID 13753435(S)-2-(Acetoxyacetyl)-1-(tert-butoxycarbonyl)pyrrolidine

Conditions

Temperature
100 °C

Procedure

(S)-1-(tert-Butoxycarbonyl)-2-(diazoacetyl)pyrrolidine (16.2 g) was dissolved in acetic acid and the mixture was heated at 100° C. for 10 minutes. The reaction mixture was allowed to cool and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with an aqueous solution of sodium bicarbonate and water in order, dried over anhydrous sodium sulfate, and concentrated to give the title compound (8.9 g).

Workup

  1. temperatureto cool
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with an aqueous solution of sodium bicarbonate and water in order
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-637431ecd20f4a328c76e3ed74ff2018
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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