Triethylamine → cis(+/-)-3-(tert-Butoxycarbonyl)amino-1-(diphenylmethyl)-2-ethylazetidine

HRID 1425389Notes

Reaction equation

HRID 1425389 reaction equation
[C:1](OC([O-])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[C:19]1([CH:25]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:26]2[CH2:29][C@H:28]([NH2:30])[C@@H:27]2[CH2:31][CH3:32])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>ClCCl.C(OCC)(=O)C>[C:4]([O:3][C:1]([NH:30][C@H:28]1[CH2:29][N:26]([CH:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C@H:27]1[CH2:31][CH3:32])=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10038572cis(+/-)-1-(Diphenylmethyl)-2-ethylazetidin-3-amineHCID 22064466Tert-butyldicarbonate

Product 1

HCID 86648819cis(+/-)-3-(tert-Butoxycarbonyl)amino-1-(diphenylmethyl)-2-ethylazetidineYield 57.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl dicarbonate (202 mg, 0.93 mmol) and triethylamine (0.27 mL, 1.93 mmol) were added to a solution of cis(±)-1-(diphenylmethyl)-2-ethylazetidin-3-amine obtained in Example (235d) (206 mg, 0.77 mmol) in dichloromethane (4 mL), followed by stirring for two hours. The reaction solution was diluted with ethyl acetate, and the organic layer was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate. Following filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1) to obtain 161 mg of the title compound as a colorless oily substance (57%).

Workup

  1. washthe organic layer was washed with water and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-d887b062fb2e407995d5457a4b3e8ec5
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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