Water → N-[2-(3,4-Difluorophenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydro-1-naphthamide

HRID 2185909ノート

反応式

HRID 2185909 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:13][NH:14][CH3:15])[CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[F:8].[C:16]1([C:26](Cl)=[O:27])[C:25]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=2[CH:19]=[CH:18][CH:17]=1.O>C(Cl)Cl.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:10][CH2:11][OH:12])[CH2:13][N:14]([CH3:15])[C:26]([C:16]2[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=3[CH:19]=[CH:18][CH:17]=2)=[O:27])[CH:5]=[CH:6][C:7]=1[F:8]

参加物

6

反応物 3

HCID 962WaterHCID 27531625,6,7,8-Tetrahydronaphthalene-1-carbonyl chlorideHCID 224526363-(3,4-Difluorophenyl)-n-methyl-4-amino-1-butanol

生成物 1

HCID 22452632N-[2-(3,4-Difluorophenyl)-4-hydroxybutyl]-N-methyl-5,6,7,8-tetrahydro-1-naphthamide収率 79%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒3 回HCID 14798Sodium Hydroxide溶媒

反応条件

温度
0 °C

実験手順

To a stirred cooled (0° C.) mixture of 3-(3,4-difluorophenyl)-N-methyl-4-amino-1-butanol (0.917 g, 4.26 mmol) in DCM (35 mL) and 1N NaOH (10 mL) was added dropwise a solution of 5,6,7,8-tetrahydro-1-naphthalenecarbonyl chloride (0.829 g, 4.26 mmol) in DCM (20 mL). The mixture was stirred at 0° C. for 2.5 h, additional H2O and DCM were added and the mixture was extracted with DCM (2×20 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. Purification by chromatography (0%, 50%, 100% EtOAc in Et2O) provided the title compound (1.25 g, 79%) as a solid. MS m/z 374 (M+H).

後処理

  1. temperatureTo a stirred cooled
  2. extractionthe mixture was extracted with DCM (2×20 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography (0%, 50%, 100% EtOAc in Et2O)

出典と根拠

ORDレコード
ord-976033e63fae491db24268a8c8b05808
出典データセット
uspto-grants-2002_06
特許番号
US06403601B1

反応ノート

読み込み中…