Methyl chloroglyoxylate → methyl oxo((phenylmethyl){[(3R)-4-(phenylmethyl)-3-morpholinyl]methyl}amino)acetate

HRID 1366559Notes

Reaction equation

HRID 1366559 reaction equation
[C:1]1([CH2:7][NH:8][CH2:9][C@@H:10]2[CH2:15][O:14][CH2:13][CH2:12][N:11]2[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)C(C)C)(C)C.Cl[C:33](=[O:38])[C:34]([O:36][CH3:37])=[O:35]>C1COCC1>[O:38]=[C:33]([N:8]([CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:9][C@@H:10]1[CH2:15][O:14][CH2:13][CH2:12][N:11]1[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:34]([O:36][CH3:37])=[O:35]

Participants

5

Reactant 3

HCID 79846Methyl chloroglyoxylateHCID 81531DiisopropylethylamineHCID 669364391-phenyl-N-{[(3R)-4-(phenylmethyl)-3-morpholinyl]methyl}methanamine

Product 1

HCID 66936387methyl oxo((phenylmethyl){[(3R)-4-(phenylmethyl)-3-morpholinyl]methyl}amino)acetateYield 107.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-phenyl-N-{[(3R)-4-(phenylmethyl)-3-morpholinyl]methyl}methanamine (3.3777 g, 11.40 mmol) in THF (114 mL) was added N,N-diisopropylethylamine (3 mL, 17.22 mmol). To the solution was added methyl chloro(oxo)acetate (1.15 mL, 12.50 mmol) dropwise via syringe, and the mixture was stirred for 3 h. The solvent was removed in vacuo, and the residue was dissolved in EtOAc (200 mL) and washed with sat. aq. NaHCO3 followed by water. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford crude methyl oxo((phenylmethyl){[(3R)-4-(phenylmethyl)-3-morpholinyl]methyl}amino)acetate (4.6881 g, >100% crude yield) as a yellow oil. LCMS: (M+H)+: 383.1.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in EtOAc (200 mL)
  3. washwashed with sat. aq. NaHCO3
  4. dry with materialThe organic phase was dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-86da69760ace47718f44a18aa848e88c
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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