Methanol → AC-Pro-ome

HRID 579825

Reaction equation

C[OH:2].[C:3]([N:6]1[CH2:10][CH2:9][CH:8]=[CH:7]1)(=[O:5])[CH3:4].[O:11]1[CH2:15]CC[CH2:12]1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:12][O:11][C:15](=[O:2])[C@@H:7]1[CH2:8][CH2:9][CH2:10][N:6]1[C:3](=[O:5])[CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

A 70 mL stainless steel high pressure reactor having a Pyrex glass liner and a magnetic stir bar was charged with 5 mL of tetrahydrofuran, 0.5 mmol of n-pendadecane internal standard, 0.5 mmol of CH3OH, 35.1 mg of (PPh3)2PdCl2, and 56.6 mg of N-acetyl-2-pyrroline. The reactor was pressurized to 1000 psi with CO at room temperature, and the reaction mixture was stirred at 100° C. for 26 hours. Thereafter, the reactor was cooled to room temperature and vented to atmospheric pressure. The product mixture was analyzed by gas chromatography, and the analysis indicated 98.4% conversion of N-acetyl-2-pyrroline and 42.8% yield of N-acetylproline methyl ester.

Workup

customA 70 mL stainless steel high pressure reactor having
customwas pressurized to 1000 psi with CO at room temperature
temperatureThereafter, the reactor was cooled to room temperature

Sources & evidence

ORD record: ord-23c5847cc75b4d75b1676b3af4447543
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04749786

Linked notes

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