tert-Butanol → HCID 54182549, compound

HRID 579830

Reaction equation

CCCCCCCCCCCCCCC.[C:16]([OH:20])([CH3:19])([CH3:18])[CH3:17].[C:21]([N:24]1[CH2:28][CH2:27][CH:26]=[CH:25]1)(=[O:23])[CH3:22].[O:29]1CCC[CH2:30]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>[C:16]([O:20][C:30](=[O:29])[C@@H:25]1[CH2:26][CH2:27][CH2:28][N:24]1[C:21](=[O:23])[CH3:22])([CH3:19])([CH3:18])[CH3:17]

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 mol of n-pentadecane internal standard, 0.5 mmol of tert-butyl alcohol, 40 mg of (PPh3)2PdCl2, and 55.5 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 21 hours. Thereafter, the reactor was cooled to room temperature and vented to atmospheric pressure. The product mixture was analyzed by gas chromatography and mass spectrometry, and the analysis indicated 98.6% conversion of N-acetyl-2-pyrroline and 1.0% yield of N-acetylproline tert-butyl 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-813b2ab7835346c8897922047801d6e1
Source dataset: uspto-grants-1988_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04749786

Linked notes

Loading…