Diketene → HCID 53468219, compound

HRID 1055225Notes

Reaction equation

HRID 1055225 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([OH:6])[CH2:2]1.[CH2:7]=[C:8]1[O:12][C:10](=[O:11])[CH2:9]1>O1CCCC1>[OH:6][C@H:3]1[CH2:4][CH2:5][N:1]([C:10](=[O:11])[CH2:9][C:8](=[O:12])[CH3:7])[CH2:2]1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 2733874(3S)-pyrrolidin-3-ol

Product 1

HCID 53468219HCID 53468219, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 21.8 g (0.25 mol) (S)-3-pyrrolidinol in 200 ml tetrahydrofuran was added dropwise to a solution of 20 g of diketene (0.24 mol) in 200 ml of tetrahydrofuran at −5 to 0° C. added. After 1 h stirring at 0° C. no more starting material was detected by thin layer chromatography. The reaction mixture was evaporated and the residue purified by column chromatography. This gave 31.35 g (0.18 mol, 77% yield) of a colorless oil.

Workup

  1. additionadded
  2. customThe reaction mixture was evaporated
  3. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-758d1142e9664b9b872b2c64585a8a84
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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