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

HRID 926267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 926267
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 86711345Methyl 2-(5-iodo-1,2,3,4-tetrahydroisoquinolin-1-yl)propanoateAusbeute 101,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-64d2f343056e43319fc34265caff880f
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284331B2

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