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

HRID 532894Notes

Reaction equation

HRID 532894 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-a86b965afe324aba963f5b1888cf739e
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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