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

HRID 501320

反応式

HRID 501320 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 21899848Ethylacetate heptane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4fe4a48a5a504448a2d574a082643679
出典データセット
uspto-grants-2010_08
特許番号
US07772252B2

関連ノート

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