Sodium Hydroxide → Methyl 2-(5-iodo-1,2,3,4-tetrahydroisoquinolin-1-yl)propanoate

HRID 926267ノート

反応式

HRID 926267 の反応式
[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]=[C:7]2[CH:12]([CH3:17])[C:13]([O:15][CH3:16])=[O:14].[BH3-]C#N.[Na+].[OH-].[Na+]>CC(O)=O>[I:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][NH:6][CH:7]2[CH:12]([CH3:17])[C:13]([O:15][CH3:16])=[O:14]

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 86711344Methyl 2-(5-iodo-3,4-dihydroisoquinolin-1-yl)propanoate

生成物 1

HCID 86711345Methyl 2-(5-iodo-1,2,3,4-tetrahydroisoquinolin-1-yl)propanoate収率 101.2%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of methyl 2-(5-iodo-3,4-dihydroisoquinolin-1-yl)propanoate (1.15 g, 3.35 mmol) in glacial AcOH (12 mL) was treated with NaBH3CN (421 mg, 6.70 mmol) at RT under N2. The mixture was stirred at RT for 16 h, and then poured onto H2O. The mixture was rendered basic with a 50% aqueous solution of NaOH and extracted with AcOEt. The combined org. phases were then dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (1.17 g) that was used as it is. UPLC-MS: MS 346.1 (M+H+); UPLC rt 0.65 min.

後処理

  1. additionpoured onto H2O
  2. extractionextracted with AcOEt
  3. dry with materialphases were then dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-64d2f343056e43319fc34265caff880f
出典データセット
uspto-grants-2016_03
特許番号
US09284331B2

反応ノート

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