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

HRID 1260235ノート

反応式

HRID 1260235 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 (2900, 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-a337fec6db594671a88a89e26a7c4f14
出典データセット
uspto-grants-2013_06
特許番号
US08470810B2

反応ノート

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