Carbon Dioxide → 1-Methyl-1-oxo-1lambda5-phosphinane-4-carboxylic acid

HRID 1863890Notes

Reaction equation

[CH3:1][P:2]1(=[O:14])[CH2:7][CH2:6][C:5](C(O)=O)([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.C(=O)=O>O>[CH3:1][P:2]1(=[O:14])[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 215 °C

Procedure

To a 50 mL microwave pressure flask equipped with a stir-bar was added 1-methyl-1-oxo-1λ5-phosphinane-4,4-dicarboxylic acid (0.25 g, 5.7 mmol) and water (20 mL) to give a suspension. The flask was sealed and heated to 215° C. over 60 seconds, at which point a pressure spike was observed. The flask was allowed to cool to room temperature then vented to release pressure from dissolved CO2. The resulting clear and colorless solution was concentrated by lyophilization to provide 1-methyl-1-oxo-1λ5-phosphinane-4-carboxylic acid in quantitative yield as a mixture of cis/trans isomers (˜2:1; identity of the favored isomer not determined). 1H NMR (400 MHz, D2O) δ ppm 2.6-2.4 (m, 1H), 2.2-1.6 (m, 8H), 1.48 (d, J=12.9 Hz, minor isomer, 1H), 1.44 (d, J=13.7 Hz, major isomer, 2H); ESMS m/z: found, 177 (M+1)+, 353 (2M+1)+.

Workup

customTo a 50 mL microwave pressure flask equipped with a stir-bar
customto give a suspension
customThe flask was sealed
temperatureto cool to room temperature
concentrationThe resulting clear and colorless solution was concentrated by lyophilization

Sources & evidence

ORD record: ord-ba9586c191e84311abb32419dadfb91e
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625880B2

Reaction notes

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