Sodium borohydride → 4,4-Dimethyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

HRID 445285ノート

反応式

HRID 445285 の反応式
[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:4][CH2:3]1.[BH4-].[Na+]>CO>[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:19])[F:20])=[CH:14][CH:13]=2)[NH:4][CH2:3]1

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 595364234,4-Dimethyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline

生成物 1

HCID 595363404,4-Dimethyl-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A 50-mL round-bottomed flask was charged with 4,4-dimethyl-1-(4-(trifluoromethyl)phenyl)-3,4-dihydroisoquinoline (2.52 g, 8.3 mmol) and dry MeOH (10 mL). After cooling down to 0° C. sodium borohydride (943 mg, 24.9 mmol) was added and the mixture was stirred at RT for 45 min. Then, the solvent was removed and the residue redissolved in EtOAc, washed with sat NaHCO3, water and dried over Na2SO4. The residue was purified by silica gel chromatography (25-35% EtOAc in hexanes) to give the title compound as a white solid. MS (ESI, positive ion) m/z: 306 (M+H).

後処理

  1. additionwas added
  2. customThen, the solvent was removed
  3. dissolutionthe residue redissolved in EtOAc
  4. washwashed
  5. dry with materialdried over Na2SO4
  6. customThe residue was purified by silica gel chromatography (25-35% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-f2c24425ee0f4b778565f1a525ae121d
出典データセット
uspto-grants-2013_07
特許番号
US08476297B2

反応ノート

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