Benzyl chloroformate → Benzyl 7-nitro-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

HRID 1524292ノート

反応式

HRID 1524292 の反応式
Cl.[N+:2]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][NH:11][CH2:12]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].C([O-])([O-])=O.[K+].[K+].Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>CCOC(C)=O.O>[CH2:25]([O:24][C:22]([N:11]1[CH2:10][CH2:9][C:8]2[C:13](=[CH:14][C:5]([N+:2]([O-:4])=[O:3])=[CH:6][CH:7]=2)[CH2:12]1)=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

参加物

6

反応物 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 135216707-Nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride

生成物 1

HCID 53419203Benzyl 7-nitro-1,2,3,4-tetrahydroisoquinoline-2-carboxylate収率 91.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 7-nitro-1,2,3,4-tetrahydroisoquinoline hydrochloride (11.0 g, 51.25 mmol) in EtOAc (150 mL) at 0° C. in an ice bath add a solution of K2CO3 (15.65 g, 113.25 mmol) in water (150 mL) followed by benzyl chloroformate (8.37 mL, 56.37 mmol) and vigorously stir the reaction at room temperature for 24 h. Separate the layers and extract the aqeuous with more EtOAc (150 mL). Wash the organics with sat. NaHCO3 (200 mL), sat. NH4Cl (200 mL) and water (200 mL), then dry (Na2SO4). Concentrate in vacuo to give 14.70 g of 7-nitro-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester as an oil which partially crystallizes.

後処理

  1. customthe reaction at room temperature for 24 h
  2. customSeparate the layers
  3. extractionextract the aqeuous with more EtOAc (150 mL)
  4. washWash the organics with sat. NaHCO3 (200 mL), sat. NH4Cl (200 mL) and water (200 mL)
  5. dry with materialdry (Na2SO4)
  6. concentrationConcentrate in vacuo

出典と根拠

ORDレコード
ord-3ae326eec657426ebaa0390190a2c4ad
出典データセット
uspto-grants-2015_07
特許番号
US09079880B2

反応ノート

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