Water → 1-Amino-1-[1-(4-chlorophenyl)cyclobutyl]-3-ethylpentan-3-ol

HRID 728278ノート

反応式

HRID 728278 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12](=[NH:20])[CH2:13][C:14]([CH2:18][CH3:19])([OH:17])[CH2:15][CH3:16])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.O.[OH-].[Na+]>O1CCCC1>[NH2:20][CH:12]([C:8]1([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)[CH2:11][CH2:10][CH2:9]1)[CH2:13][C:14]([CH2:15][CH3:16])([OH:17])[CH2:18][CH3:19]

参加物

5

反応物 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 198237421-[1-(4-Chlorophenyl)cyclobutyl]-3-ethyl-1-iminopentan-3-ol

生成物 1

HCID 198237701-Amino-1-[1-(4-chlorophenyl)cyclobutyl]-3-ethylpentan-3-ol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

A solution of 1-[1-(4-chlorophenyl)cyclobutyl]-3-ethyl-1-iminopentan-3-ol (1.6 g) in dry tetrahydrofuran (20 ml) was treated under nitrogen with boranetetrahydrofuran complex (1M solution in tetrahydrofuran 10 ml) and the mixture was heated under reflux for 24 hours. The mixture was cooled in ice and water and then 2N sodium hydroxide solution were added. The resulting mixture was extracted with ether and the extracts were washed, dried and evaporated to give 1-amino-1-[1-(4-chlorophenyl)cyclobutyl]-3-ethylpentan-3-ol which was then converted into the corresponding dimethylamino compound by heating a mixture of the primary amine (1.5 g), 98% formic acid (4 ml) and 37-40% aqueous formaldehyde (2 ml) at 90°-95° C. for 16 hours. The reaction mixture was cooled and poured into a mixture of 16N sodium hydroxide solution (7 ml) and ice. The mixture was extracted with ether and the extract washed, dried and evaporated to give a residue which was dissolved in ether. Addition of a solution of maleic acid in ether gave 1-[1-(4-chlorophenyl)cyclobutyl]-1-dimethylamino-3-ethylpentan-3-ol maleate (m.p. 110°-111° C.).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 hours
  3. temperatureThe mixture was cooled in ice
  4. extractionThe resulting mixture was extracted with ether
  5. washthe extracts were washed
  6. customdried
  7. customevaporated

出典と根拠

ORDレコード
ord-f91dda78e00644f1ada4d4690f2d919b
出典データセット
uspto-grants-1991_09
特許番号
US05047432

反応ノート

読み込み中…