Diethyl Ether → Methyl 2-benzyl-3-benzyloxy-3-[(4-morpholinyl)carbonyl]propionate

HRID 1535068Notes

Reaction equation

[CH2:1]([O:8][CH2:9][C:10]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br[CH:29]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:30]([O:32][CH3:33])=[O:31].CCOCC>C1COCC1.[Cl-].[Na+].O>[CH2:34]([CH:29]([CH:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:10]([N:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)=[O:11])[C:30]([O:32][CH3:33])=[O:31])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A -78° C. solution of N-(benzyloxyacetyl)morpholine (1 g, 8.5 mmol) in THF (25 mL) was treated with potassium bis(trimethylsilyl)amide (17 mL of a 0.5M solution). After stirring for 10 min at -78° C., a solution of methyl 2-bromo-3-phenylpropionate (8.5 mmol) in THF (5 mL) was added dropwise. Stirring at -78° C. for 30 min was followed by warming to 0° C. The reaction was then distributed between ether and brine solution. The organic layer was washed with brine and dried over MgSO4. Evaporation and flash chromatography on silica gel gave the desired product in 63% yield

Workup

stirringStirring at -78° C. for 30 min
temperatureby warming to 0° C
washThe organic layer was washed with brine
dry with materialdried over MgSO4
customEvaporation and flash chromatography on silica gel

Sources & evidence

ORD record: ord-43fdebd0839d4ce4aa090b037a50dd9a
Source dataset: uspto-grants-1992_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05091575

Reaction notes

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