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

HRID 532894노트

반응식

HRID 532894 반응식
[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+].N#N.[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]

참가 물질

6

반응물 4

HCID 947NitrogenHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 86711344Methyl 2-(5-iodo-3,4-dihydroisoquinolin-1-yl)propanoate

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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 RTunder 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.

후처리

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

출처 및 근거

ORD 기록
ord-a86b965afe324aba963f5b1888cf739e
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08853203B2

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