Sodium Bicarbonate → 2-(4-Benzyl-morpholin-2-yl)-1,3-bis-(2-methoxy-phenyl)-propan-2-ol

HRID 30331Notes

Reaction equation

HRID 30331 reaction equation
C(O[C:4]([CH:6]1[O:11][CH2:10][CH2:9][N:8]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7]1)=[O:5])C.[CH3:19][O:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[CH2:23][Mg]Cl.[C:30](=[O:33])(O)[O-].[Na+]>O1CCCC1>[CH2:12]([N:8]1[CH2:9][CH2:10][O:11][CH:6]([C:4]([OH:5])([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:33][CH3:30])[CH2:23][C:22]2[CH:26]=[CH:27][CH:28]=[CH:29][C:21]=2[O:20][CH3:19])[CH2:7]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 15651196Ethyl 4-benzylmorpholine-2-carboxylateHCID 178489472HCID 178489472, compound

Product 1

HCID 588548932-(4-Benzyl-morpholin-2-yl)-1,3-bis-(2-methoxy-phenyl)-propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Add a solution of 4-benzyl-morpholine-2-carboxylic acid ethyl ester (1.12 g, 4.49 mmol) in tetrahydrofuran (5 mL) to a stirred solution of 2-methoxybenzylmagnesium chloride (54 mL, 0.25M solution in tetrahydrofuran, commercially available from Rieke Metals) at −10° C. under nitrogen atmosphere. After 1 hour, add a saturated aqueous solution of sodium bicarbonate and extract with diethyl ether. Combine the organic layers and extract with brine, dry over magnesium sulfate, filter, and concentrate under reduced pressure to give a residue to be taken forward without further purification. MW 447.58; C28H33NO4; LCMS (12 minute method):m/z)=448.2 [M+H]+) RT 4.8 min.

Workup

  1. customat −10° C.
  2. extractionextract with diethyl ether
  3. extractionextract with brine
  4. dry with materialdry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customto give a residue
  8. customto be taken forward without further purification
  9. customLCMS (12 minute method)
  10. customRT 4.8 min.

Sources & evidence

ORD record
ord-8ef79c5512454b1b9d18808a10568d53
Source dataset
uspto-grants-2008_09
Patent number
US07423037B2

Reaction notes

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