Thionyl Chloride → HCID 59333778, compound

HRID 1930720Notes

Reaction equation

HRID 1930720 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]([OH:11])=O.S(Cl)(Cl)=O.O=C1CCCN1CCC(Cl)=O.[O:27]1[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]1>>[O:11]=[C:9]([CH:29]1[C:30](=[O:33])[CH2:31][CH2:32][O:27][CH2:28]1)[CH2:8][CH2:7][N:3]1[CH2:4][CH2:5][CH2:6][C:2]1=[O:1]

Participants

5

Reactant 4

HCID 24386Thionyl ChlorideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 31466882-Oxo-1-pyrrolidinepropanoic acidHCID 12843799HCID 12843799, compound2×

Product 1

HCID 59333778HCID 59333778, compoundYield 25.6%

Procedure

3-(2-Oxopyrrolidin-1-yl)propanoic acid (519 mg, 3.3 mmol) was heated to reflux in thionyl chloride (0.365 ml, 5.00 mmol) for 30 min. The excess of thionyl chloride was evaporated and the product, (3-(2-oxopyrrolidin-1-yl)propanoyl chloride (3.3 mmol)) used as such in the next step. 1-(3-oxo-3-(4-oxotetrahydro-2H-pyran-3-yl)propyl)pyrrolidin-2-one (202 mg, 15%) was synthesised from dihydro-2H-pyran-4(3H)-one (0.462 ml, 5.00 mmol) and 3-(2-oxopyrrolidin-1-yl)propanoyl chloride (3.3 mmol) by the general procedure for the preparation of diketones.

Workup

  1. customThe excess of thionyl chloride was evaporated

Sources & evidence

ORD record
ord-e4ca1242ece74fbbbd97f1b2c853f409
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

Loading…