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

HRID 1260235노트

반응식

HRID 1260235 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-a337fec6db594671a88a89e26a7c4f14
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08470810B2

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