Water → 7-Methylthiomethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester

HRID 412521ノート

反応式

HRID 412521 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([OH:18])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:21][S:22][CH2:23]Cl.O>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][C:12]([O:18][CH2:21][S:22][CH3:23])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 4

HCID 962WaterHCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 10562576Tert-butyl 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

生成物 1

HCID 600641317-Methylthiomethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 7-hydroxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid tert-butyl ester (13 g) in dirnethylformamide (100 ml) was added 60% sodium hydride (2.5 g) under an argon atmosphere, and the mixture was stirred at room temperature for 30 minutes. Then, chloromethyl methyl sulfide (5.2 ml) was dropwise added with ice-cooling, and the mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was poured into water, extracted with ethyl acetate and washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:acetone=20:1-10:1) and dried under reduced pressure to give the title compound (9.6 g).

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred at room temperature overnight
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washwashed successively with water and saturated brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customthe obtained residue was purified by silica gel column chromatography (hexane:acetone=20:1-10:1)
  9. customdried under reduced pressure

出典と根拠

ORDレコード
ord-03dc22aa97fb456fb5c6ec14aa3dd2b3
出典データセット
uspto-grants-2003_05
特許番号
US06562828B1

反応ノート

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