N,N,2-trimethylaziridine-1-carboxamide → HCID 178458364, compound

HRID 2254491Notes

Reaction equation

C([Li])CCC.[CH2:6]([O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=1[F:17])[CH2:7][CH3:8].[CH2:18]([C@H:21]1[CH2:26][CH2:25][C@H:24]([CH2:27][CH2:28][C@H:29]2[CH2:34][CH2:33][C@H:32]([CH2:35][CH2:36]I)[CH2:31][CH2:30]2)[CH2:23][CH2:22]1)[CH2:19][CH3:20].CC1N(C(N(C)C)=O)C1>CCCCCC.O1CCCC1>[CH2:6]([O:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:36][CH2:35][C@H:32]2[CH2:33][CH2:34][C@H:29]([CH2:28][CH2:27][C@H:24]3[CH2:23][CH2:22][C@H:21]([CH2:18][CH2:19][CH3:20])[CH2:26][CH2:25]3)[CH2:30][CH2:31]2)=[C:12]([F:16])[C:11]=1[F:17])[CH2:7][CH3:8]

Participants

Conditions

Temperature: -40 °C

Procedure

65 ml of a solution of 0.1 mol of n-butyllithium in hexane is added at -100° C. to a mixture of 0.1 mol of 4- propoxy-2,3-difluorobenzene, 0.09 mol of potassium tert.butylate and 250 ml of tetrahydrofuran. After stirring for 10 minutes a mixture of 0.1 mole of trans-4-(trans-4-propylcyclohexylethyl)-cyclohexylethyl iodide, 0.1 mol of N,N-dimethylpropyleneurea and 100 ml of tetrahydrofuran is added to the mixture. Stirring for 1 hour at -85° C., warming up to -40° C. and working up in the customary manner gives trans-4-(2-(4-propoxy-2,3-difluorophenyl)-ethyl)-1-(2-(trans-4-propylcyclohexyl)ethyl)-cyclohexane.

Workup

additionis added to the mixture
stirringStirring for 1 hour at -85° C.

Sources & evidence

ORD record: ord-4ce1ec3aecaf4d5aac8a5addbb4e79b5
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05236620

Reaction notes

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