Phthalylglycine aldehyde → N-(2-Aminoethyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline

HRID 379523ノート

反応式

HRID 379523 の反応式
[CH3:1][O:2][C:3]1[C:12]([O:13][CH3:14])=[C:11]2[C:6]([CH2:7][CH2:8][NH:9][CH2:10]2)=[CH:5][CH:4]=1.C1(=O)[N:19](CC=O)[C:18](=O)[C:17]2=CC=CC=C12.CC([O-])=O.[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[NH2:19][CH2:18][CH2:17][N:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:12]([O:13][CH3:14])[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:10]1

参加物

6

反応物 4

HCID 76201Phthalylglycine aldehydeHCID 1796067,8-Dimethoxy-1,2,3,4-tetrahydroisoquinolineHCID 517045Sodium AcetateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 15884736N-(2-Aminoethyl)-7,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of 7,8dimethoxy-1,2,3,4-tetrahydroisoquinoline (421 mg, 2.2 mmol), 2-phthalimidoacetaldehyde (410 mg, 2.2 mmol) and NaOAc (180 mg, 2.2 mmol) in 27 mL of CH2Cl2 was added 690 mg (3.25 mmol) of NaBH(OAc)3 in small portions. After stirring 1 hour at room temperature, the reaction mixture was diluted with CH2Cl2 and washed with a saturated Na2CO3 solution and brine. The residue obtained after evaporation of CH2Cl2 was dissolved in 25 mL of EtOH and treated with 1.2 mL of hydrazine hydrate overnight. The reaction mixture was then filtered and evaporated to give 510 mg (100%) of the title compound; MS m/e 327 (M+1).

後処理

  1. washwashed with a saturated Na2CO3 solution and brine
  2. customThe residue obtained
  3. customafter evaporation of CH2Cl2
  4. dissolutionwas dissolved in 25 mL of EtOH
  5. additiontreated with 1.2 mL of hydrazine hydrate overnight
  6. filtrationThe reaction mixture was then filtered
  7. customevaporated

出典と根拠

ORDレコード
ord-d1c0c9b4ab2b45c485c159650512548b
出典データセット
uspto-grants-2001_10
特許番号
US06300316B1

反応ノート

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