3-Pentyl-3-phenylazetidine oxalate → 3-Cyclohexyl-3-pentylazetidine oxalate

HRID 540401Notes

Reaction equation

[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH2:7]([C:12]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:15][NH:14][CH2:13]1)[CH2:8][CH2:9][CH2:10][CH3:11]>O.C1COCC1.[Rh]>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH:16]1([C:12]2([CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:13][NH:14][CH2:15]2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

Conditions

Temperature: 80 °C

Procedure

254 mg of rhodium-on-alumina at 5% are added to 652 mg (2.62 mmol) of 3-pentyl-3-phenylazetidine oxalate (cf.) in 13 ml of water and 6.5 ml of THF. The medium is placed under a hydrogen atmosphere at 6 bar of pressure and heated at 80° C. After 23 hours, the reaction medium is filtered through celite and the solvents are evaporated off. 0.43 g of 3-cyclohexyl-3-pentylazetidine oxalate is obtained with a yield of 64%.

Workup

filtrationthe reaction medium is filtered through celite
customthe solvents are evaporated off

Sources & evidence

ORD record: ord-78e56b92a36c4b2fa7d4b5e4dbfa2efe
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871187B2

Reaction notes

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