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

HRID 1409011Notes

Reaction equation

HRID 1409011 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-f1756fe8ab384db6bf6a22e14552ae35
Source dataset
uspto-grants-2014_12
Patent number
US08921354B2

Reaction notes

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