Trifluoroacetic acid → 1-(3-(4-Nitrophenyl)azetidin-1-yl)propan-1-one

HRID 2262620Notes

Reaction equation

HRID 2262620 reaction equation
C(O[C:6]([N:8]1[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[CH2:9]1)=[O:7])(C)(C)C.[C:21](O)([C:23](F)(F)F)=O.C(Cl)(=O)CC.C(N(CC)CC)C>C(Cl)Cl.C1COCC1>[N+:18]([C:15]1[CH:14]=[CH:13][C:12]([CH:10]2[CH2:9][N:8]([C:6](=[O:7])[CH2:21][CH3:23])[CH2:11]2)=[CH:17][CH:16]=1)([O-:20])=[O:19]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 57470079HCID 57470079, compound

Product 1

HCID 574700801-(3-(4-Nitrophenyl)azetidin-1-yl)propan-1-oneYield 87%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Using the same procedure as described in 46.4, 3-(4-nitro-phenyl)-azetidine-1-carboxylic acid tert-butyl ester was deprotected with TFA (15 ml) in CH2Cl2 (100 ml) and the resulting amine treated with propionyl chloride (290 μl, 3.31 mmol) and triethylamine (470 μl, 3.37 mmol) in THF (80 ml). Purification of the crude product by flash column chromatography (heptane:ethyl acetate, 1:1) provides the title compound (570 mg, 87% for two steps) as a brown oil.

Workup

  1. customPurification of the crude product by flash column chromatography (heptane:ethyl acetate, 1:1)

Sources & evidence

ORD record
ord-f748c72f6a9a47aa8063518cc64ffc1e
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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