tert-Butanol → (1R,2S)-2-tert-Butoxycarbonylcyclopropanecarboxylic acid

HRID 1662066Notes

Reaction equation

HRID 1662066 reaction equation
[C@@H:1]12[CH2:6][C@@H:5]1[C:4](=[O:7])[O:3][C:2]2=[O:8].[CH3:9][C:10]([OH:13])([CH3:12])[CH3:11]>>[C:10]([O:13][C:4]([C@H:5]1[CH2:6][C@H:1]1[C:2]([OH:8])=[O:3])=[O:7])([CH3:12])([CH3:11])[CH3:9]

Participants

3

Reactant 2

HCID 6386tert-ButanolHCID 12688062(1r,5s)-3-Oxabicyclo[3.1.0]hexane-2,4-dione

Product 1

HCID 53929811(1R,2S)-2-tert-Butoxycarbonylcyclopropanecarboxylic acid

Conditions

Temperature
110 °C

Procedure

A mixture of rel-(1R,5S)-3-oxabicyclo[3.1.0]hexane-2,4-dione (1.1 g) and 2-methyl-2-propanol (10 ml) was stirred at 110° C. for 2.5 days. The reaction mixture was concentrated under reduced pressure to obtain rel-(1R,2S)-2-(tert-butoxycarbonyl)cyclopropanecarboxylic acid (1.8 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3e6a49a9f72f40788d8e1c181141661a
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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