Ethyl Acetate → HCID 67980521、化合物

HRID 1622305ノート

反応式

HRID 1622305 の反応式
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4][NH:3]1.[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C.O>[Br:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:3]2[CH2:4][CH2:5][C:6]3[C:11](=[CH:10][CH:9]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:7]=3)[CH2:2]2)=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 685274-Bromobenzyl bromideHCID 42614607Methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride

生成物 1

HCID 67980521HCID 67980521、化合物収率 104.5%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of methyl 1,2,3,4-tetrahydroisoquinoline-6-carboxylate hydrochloride (500.0 mg, 2.00 mmol) in DMF (17.0 mL) was added 4-bromobenzylbromide (604 mg, 2.42 mmol) and K2CO3 (910 mg, 6.59 mmol). The resulting mixture was stirred overnight at rt. EtOAc and water were added, and the phases were separated. The organic phase was dried over Na2SO4, filtered and concentrated. The resulting residue was purified by column chromatography (SiO2, 0-40% EtOAc in hexane) to give methyl 2-(4-bromobenzyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate (753 mg, 100%). LC-MS: (FA) ES+ 361; 1H NMR (300 MHz, CDCl3) δ 7.86-7.70 (m, 2H), 7.46 (dd, J=8.7, 2.1 Hz, 2H), 7.36-7.21 (m, 2H), 7.04 (d, J=8.0 Hz, 1H), 3.89 (d, J=3.8 Hz, 3H), 3.64 (s, 4H), 2.93 (t, J=5.8 Hz, 2H), 2.83-2.64 (m, 2H).

後処理

  1. customthe phases were separated
  2. dry with materialThe organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue was purified by column chromatography (SiO2, 0-40% EtOAc in hexane)

出典と根拠

ORDレコード
ord-15956912804947f5a3d512b5a398d003
出典データセット
uspto-grants-2014_07
特許番号
US08778931B2

反応ノート

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