Hydrochloric Acid → 4-[1-(3-bromo-4-methyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic Acid tert-butyl Ester

HRID 1986914ノート

反応式

HRID 1986914 の反応式
Cl.[OH-:2].[NH4+:3].[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([C:19]2[S:20][CH:21]=[C:22]([CH3:25])[C:23]=2[Br:24])=O)[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].Cl>N1C=CC=CC=1>[C:4]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([C:19]2[S:20][CH:21]=[C:22]([CH3:25])[C:23]=2[Br:24])=[N:3][OH:2])[CH2:13][CH2:12]1)=[O:10])([CH3:7])([CH3:6])[CH3:5]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 13908798HCID 13908798、化合物HCID 588177114-[1-(3-Bromo-4-methyl-thiophen-2-yl)-methanoyl]-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 724345734-[1-(3-bromo-4-methyl-thiophen-2-yl)-1-hydroxyimino-methyl]-piperidine-1-carboxylic Acid tert-butyl Ester

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
70 °C

実験手順

Add ammonium hydroxide hydrochloride (50.68 mmol, 3.52 g, 2.00 equivalents) to a stirred solution of 4-[1-(3-bromo-4-methyl-thiophen-2-yl)-methanoyl]-piperidine-1-carboxylic acid tert-butyl ester (25.54 mol, 9.84 9, 1.00 equivalents) in pyridine (47.5 mL). Stir at room temperature overnight and at 70° C. for 4 hours. Cool the reaction mixture and add hydrochloric acid (3 M solution, 115 mL). Extract the reaction mixture with dichloromethane (115 mL), filter the organic layer, wash with water (100 mL), dry over magnesium sulfate, filter and evaporate. Recrystallize the resulting residue from toluene to yield a white solid (4.84 9). LC/MS (APCl), m/e 403 (MH+), retention time 2 min. 32 sec. Condition I.

後処理

  1. temperatureCool the reaction mixture
  2. extractionExtract the reaction mixture with dichloromethane (115 mL)
  3. filtrationfilter the organic layer
  4. washwash with water (100 mL)
  5. dry with materialdry over magnesium sulfate
  6. filtrationfilter
  7. customevaporate
  8. customRecrystallize the resulting residue from toluene
  9. customto yield a white solid (4.84 9)
  10. custom32 sec

出典と根拠

ORDレコード
ord-c7abfad3610849669c669e3b7bb184fc
出典データセット
uspto-grants-2009_06
特許番号
US07550469B2

反応ノート

読み込み中…