Water → 4-[(2-Fluoro-3-trifluoromethylphenyl)-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 501320

반응식

HRID 501320 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[C:16]=2[F:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:28][OH:29].N1C=CC=CC=1.O>C(OCC)(=O)C.CCCCCCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[C:16]=2[F:25])=[N:28][OH:29])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 962WaterHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 588175404-(2-Fluoro-3-trifluoromethyl-benzoyl)-piperidine-1-carboxylic acid tert-butyl ester

생성물 1

HCID 724345674-[(2-Fluoro-3-trifluoromethylphenyl)-hydroxyimino-methyl]-piperidine-1-carboxylic acid tert-butyl ester수율 91%

시약·촉매·용매 1

HCID 21899848Ethylacetate heptane용매

실험 절차

A mixture of 4-(2-Fluoro-3-trifluoromethyl-benzoyl)-piperidine-1-carboxylic acid tert-butyl ester (9.00 g, 24.0 mmol), hydroxylamine hydrochloride (2.00 g, 28.8 mmol) and pyridine (50 mL) was stirred at room temperature under nitrogen overnight. The yellow reaction solution was poured into cold water (500 mL) and the mixture aged at 0° C. for 1 h. The product was collected by filtration, washed with water, and dried under vacuum at 50° C. to afford 9.54 g of a while solid. Trituration of the solid with hot 25% ethyl acetate/heptane afforded 8.50 g (91%) of the desired product as a white solid. Proton NMR showed product to be a 3.8 to 1 mixture of isomers.

후처리

  1. waitthe mixture aged at 0° C. for 1 h
  2. filtrationThe product was collected by filtration
  3. washwashed with water
  4. customdried under vacuum at 50° C.
  5. customto afford 9.54 g of a while solid

출처 및 근거

ORD 기록
ord-4fe4a48a5a504448a2d574a082643679
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772252B2

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