Ammonia → cis(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-amine

HRID 1425388Notes

Reaction equation

[NH3:1].CS(O[C@H:7]1[CH2:10][N:9]([CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@H:8]1[CH2:24][CH3:25])(=O)=O>C(O)(C)C>[C:12]1([CH:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:9]2[CH2:10][C@H:7]([NH2:1])[C@@H:8]2[CH2:24][CH3:25])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 70 °C

Procedure

28% aqueous ammonia (1.2 ml) was added to a solution of cis(±)-1-(diphenylmethyl)-2-ethylazetidin-3-yl methanesulfonate obtained in Example (235c) (315 mg, 0.91 mmol) in isopropanol (2 mL), and the mixture was stirred at 70° C. for four hours. The reaction solution was concentrated under reduced pressure. Then, saturated aqueous sodium bicarbonate solution was added to the resulting residue, followed by extraction with chloroform. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. Thereafter, the filtrate was concentrated under reduced pressure to obtain 206 mg of the title compound as a pale yellow oily substance (85%).

Workup

concentrationThe reaction solution was concentrated under reduced pressure
additionThen, saturated aqueous sodium bicarbonate solution was added to the resulting residue
extractionfollowed by extraction with chloroform
dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationThereafter, the filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-953f7b320d6d46c0b87096203da91b7c
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927588B2

Reaction notes

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