Ethylene Glycol → Benzyl 1,4-dioxa-7-azaspiro[4.4]nonane-7-carboxylate

HRID 1052162Notes

Reaction equation

HRID 1052162 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[CH2:17](O)[CH2:18][OH:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[O:19]1[C:2]2([CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[O:8])[CH2:3]2)[O:1][CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 5612031-N-Cbz-3-pyrrolidinone

Product 1

HCID 15165037Benzyl 1,4-dioxa-7-azaspiro[4.4]nonane-7-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of benzyl 3-oxopyrrolidine-1-carboxylate (2.00 g), ethane-1,2-diol (2.85 mL), p-toluenesulfonic acid monohydrate (10 mg) and toluene (20 mL) was stirred with heating in a Dean-Stark apparatus at 120° C. for 6 hr. The mixture was allowed to cool to room temperature, diluted with ethyl acetate (10 mL), washed successively with water (5 mL×2) and brine (5 mL), and dried over anhydrous sodium sulfate. Insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.1 g) as a pale-yellow liquid.

Workup

  1. temperatureto cool to room temperature
  2. washwashed successively with water (5 mL×2) and brine (5 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customInsoluble material was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c0b3466aa5474609bcee973876f6439f
Source dataset
uspto-grants-2016_07
Patent number
US09388195B2

Reaction notes

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