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

HRID 1248827Notes

Reaction equation

HRID 1248827 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:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13](=[O:17])[CH2:14][O:21][C:18](=[O:20])[CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

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

Procedure

A solution of 1.00 g of the diazoketone product of Example 1 in acetic acid (15 ml) was refluxed for 10 minutes. The mixture was cooled, filtered and the acetic acid removed under reduced pressure to give (S)-1-t-butoxycarbonyl-2-(2-acetoxy-1-oxoethyl)-pyrrolidine, which was purified by chromatography on silica gel eluting with 3:1-hexane; ethyl acetate (Rf =0.3).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. customthe acetic acid removed under reduced pressure

Sources & evidence

ORD record
ord-e114660c934e47d997b8bbb3ae148300
Source dataset
uspto-grants-1986_12
Patent number
US04626545

Reaction notes

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