Acetic Acid → Methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-[(1Z)-3-(4-morpholinyl)-1-propen-1-yl]benzoate

HRID 1623741Notes

Reaction equation

HRID 1623741 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]\[CH:22]=O)=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.ClCCl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][O:9][C:10]2[CH:19]=[CH:18][C:17](/[CH:20]=[CH:21]\[CH2:22][N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86668209Methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-[(1Z)-3-oxo-1-propen-1-yl]benzoate

Product 1

HCID 67107584Methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-[(1Z)-3-(4-morpholinyl)-1-propen-1-yl]benzoate

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-[(1Z)-3-oxo-1-propen-1-yl]benzoate (may be prepared as described in Description 122; 163 mg, 0.52 mmol) in 1,2-dichloroethane (10 ml) was added morpholine (0.05 ml, 0.52 mmol) and acetic acid (0.03 ml, 0.52 mmol). The solution was stirred for 3 hours then sodium triacetoxyborohydride (165 mg, 0.78 mmol) was added and stirred for one hour. Saturated NaHCO3 solution (10 ml) was added and the mixture was stirred for 15 minutes. Dichloromethane (10 ml) was added and the organic layer was separated, dried (MgSO4) and the solvent removed in vacuo to yield the title compound as a yellow gum. 197 mg.

Workup

  1. stirringstirred for one hour
  2. stirringthe mixture was stirred for 15 minutes
  3. customthe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-82869864ec1d4a9b964ec6dd0785639f
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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