Sodium Hydroxide → 5-(3,5-Bis-trifluoromethyl-benzylamino)-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester

HRID 2353862ノート

反応式

HRID 2353862 の反応式
[CH:1]([O:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][C:10](=O)[C:9]2[CH:15]=[CH:16][CH:17]=[CH:18][C:8]1=2)=[O:6])([CH3:3])[CH3:2].[F:19][C:20]([F:34])([F:33])[C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[CH2:24][NH2:25].[BH4-].[Na+].[OH-].[Na+]>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH:1]([O:4][C:5]([N:7]1[CH2:13][CH2:12][CH2:11][CH:10]([NH:25][CH2:24][C:23]2[CH:26]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:28]=[C:21]([C:20]([F:19])([F:33])[F:34])[CH:22]=2)[C:9]2[CH:15]=[CH:16][CH:17]=[CH:18][C:8]1=2)=[O:6])([CH3:3])[CH3:2]

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 4311764Sodium borohydrideHCID 68680367Isopropyl 5-oxo-2,3,4,5-tetrahydro-1H-benzo[b]azepine-1-carboxylate

生成物 1

HCID 866160625-(3,5-Bis-trifluoromethyl-benzylamino)-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 887Methanol溶媒

実験手順

A mixture of 5-Oxo-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester (283 mg, 1.14 mmol), 3,5-Bis(trifluoromethyl)benzylamine (304 mg, 1.25 mmol) and titanium(IV) isopropoxide (0.43 ml, 1.43 mmol) was stirred at room temperature for 6 hours. The mixture was diluted with methanol (5 ml) and treated with sodium borohydride (65 mg, 1.71 mmol), then stirred at room temperature for 18 hours. The mixture was treated with 0.1N NaOH (25 ml) and stirred for 10 minutes, then filtered through Celite. The filtered residue washed successively with diethyl ether and dichloromethane. The filtrate was transferred to a separatory funnel and the organic layer was separated, dried (Na2SO4) and concentrated to provide crude 5-(3,5-Bis-trifluoromethyl-benzylamino)-2,3,4,5-tetrahydro-benzo[b]azepine-1-carboxylic acid isopropyl ester, which was elaborated without purification.

後処理

  1. stirringstirred at room temperature for 18 hours
  2. stirringstirred for 10 minutes
  3. filtrationfiltered through Celite
  4. washThe filtered residue washed successively with diethyl ether and dichloromethane
  5. customThe filtrate was transferred to a separatory funnel
  6. customthe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-c5ee00e63ac8466fab8c7ec02f300f4b
出典データセット
uspto-grants-2010_07
特許番号
US07749992B2

反応ノート

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