Water → HCID 69886263, compound

HRID 1245302Notes

Reaction equation

HRID 1245302 reaction equation
[Al+3].[Cl-].[Cl-].[Cl-].[NH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.C(OC([N:18]1[C:23](=[O:24])[CH:22]2[CH:20]([CH:21]2[C:25]([O-:27])=[O:26])[CH:19]1[C:28]([O-:30])=[O:29])=O)(C)(C)C.O>C(Cl)Cl>[C:25]([CH:21]1[CH:22]([C:23]([N:5]2[CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)=[O:24])[CH:20]1[CH:19]([C:28]([OH:30])=[O:29])[NH2:18])([OH:27])=[O:26]

Participants

6

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 6451240Aluminum(III) ChlorideHCID 21911181HCID 21911181, compound

Product 1

HCID 69886263HCID 69886263, compoundYield 112.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of AlCl3 (73 mg, 0.54 mmol) in dry CH2Cl2 (3 mL) at 0° C., morpholine (90 μl, 1.04 mmol) in dry CH2Cl2 (3 mL) was added dropwise. The mixture was stirred at room temperature for 20 min, and then ethyl (1SR, 2SR, 5RS, 6RS) 3-tert-butoxycarbonyl-4-oxo-3-azabicyclo[3.1.0]hexane-2,6-dicarboxylate (143 mg, 0.41 mmol) in dry CH2Cl2 (1 mL) was added. After stirring at room temperature for 1 h, a mixture of ice and water was added. The layers were separated and the aqueous phase was extracted with CH2Cl2. The combined organic layers were dried over MgSO4 and the solvent removed under reduced pressure. The residue was purified by flash chromatography (hexane/ethyl acetate 1/1) to give 126 mg of the desired compound (70% yield).

Workup

  1. stirringAfter stirring at room temperature for 1 h
  2. additionwas added
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with CH2Cl2
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by flash chromatography (hexane/ethyl acetate 1/1)

Sources & evidence

ORD record
ord-a38d0e8ff54e4101b6952db4f870d953
Source dataset
uspto-grants-2006_10
Patent number
US07125871B2

Reaction notes

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