Acetic Acid → (3-Morpholin-4-yl-propylamino)acetic acid ethyl ester

HRID 1362086Notes

Reaction equation

HRID 1362086 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[CH:12]=O.CC(O)=O.[BH3-]C#N.[Na+]>CO.C([O-])(O)=O.[Na+]>[CH2:16]([O:15][C:11](=[O:14])[CH2:12][NH:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)[CH3:17]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 61055N-(3-Aminopropyl)morpholineHCID 70211Ethyl oxoacetateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 43236854(3-Morpholin-4-yl-propylamino)acetic acid ethyl esterYield 47.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 4-(3-aminopropyl)morpholine (10.0 mL, 68.4 mmol) in MeOH (180 mL) was cooled in an ice bath and treated with ethyl glyoxylate (50% solution in toluene, 20.0 mL, 98.0 mmol) and HOAc (12 mL). After stirring for 15 min, NaBH3CN (4.81 g, 76.5 mmol) was added and the mixture was allowed to stir at 0° C. for 2 h. The mixture was diluted with saturated aqueous NaHCO3 (500 mL) and then extracted with EtOAc (5×300 mL) followed by CH2Cl2 (9×200 mL). The combined CH2Cl2 layers were dried over Na2SO4, filtered and the solvent was removed in vacuo to give the title compound (7.44 g, 47%) as a colorless oil: MS (ESI) m/e 231 (M+H)+.

Workup

  1. stirringto stir at 0° C. for 2 h
  2. extractionextracted with EtOAc (5×300 mL)
  3. dry with materialThe combined CH2Cl2 layers were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f97740b7bed4432288fe7050695926f2
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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