Acetic Acid → HCID 54191233, compound

HRID 850625Notes

Reaction equation

HRID 850625 reaction equation
Cl.[Br:2][C:3]1[N:8]=[C:7]([CH2:9][CH2:10][CH2:11][NH2:12])[CH:6]=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.C(O)(=O)C.[C:26]([O:30][CH2:31][CH3:32])(=[O:29])[CH:27]=O.[BH3-]C#N.[Na+].C1COCC1>CO>[CH2:31]([O:30][C:26](=[O:29])[CH2:27][NH:12][CH2:11][CH2:10][CH2:9][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([Br:2])[N:8]=1)[CH3:32]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 70211Ethyl oxoacetateHCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 19363661HCID 19363661, compound

Product 1

HCID 54191233HCID 54191233, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(6-bromo-pyridin-2-yl)propylamine 20-4 (25.6 g, 89.1 mmol), diisopropylethylamine (46.5 mL, 267 mmol), acetic acid (28 mL, 490 mmol), and ethyl glyoxylate (10.9 g, 107 mmol) in 200 ml of methanol was stirred at room temperature for one hour. A 1M solution of NaCNBH3 in THF (98.0 mL, 98.0 mmol) was added slowly with a syringe pump over 4 hours. The resulting solution was stirred for 12 hours, after which the solvent was removed in vacuo and the residue taken up in chloroform and filtered. The solution was then washed with 10% Na2CO3, dried over Na2SO4, and the solvent removed in vacuo to give the crude amine. The crude product was purified by silica gel chromatography (7% MeOH/CHCl3) to give 20-5 in a 3:2 mixture of ethyl and methyl esters.

Workup

  1. customafter which the solvent was removed in vacuo
  2. filtrationfiltered
  3. washThe solution was then washed with 10% Na2CO3
  4. dry with materialdried over Na2SO4
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ba4a9d14e53f4dedbc095db9576bc8ac
Source dataset
uspto-grants-2000_01
Patent number
US06017926

Reaction notes

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