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

HRID 2262620ノート

反応式

HRID 2262620 の反応式
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]

参加物

7

反応物 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 57470079HCID 57470079、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-f748c72f6a9a47aa8063518cc64ffc1e
出典データセット
uspto-grants-2010_12
特許番号
US07851463B2

反応ノート

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