p-Toluenesulfonic acid → HCID 15117324, compound

HRID 1029675Notes

Reaction equation

HRID 1029675 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH:13]([OH:15])[CH3:14])[C:9]1=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([CH:13]([O:15][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22][O:17]2)[CH3:14])[C:9]1=[O:16])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 15117323HCID 15117323, compound

Product 1

HCID 15117324HCID 15117324, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-t-butyloxycarbonyl-3-(1-hydroxyethyl)-2-oxopyrrolidine (15 g) in dichlormethane (200 ml) were added 3,4-dihydro-2H-pyran (11.9 ml) and p-toluenesulfonic acid (1.2 g) at 0° C. After stirring for 1 hour at the same temperature, the solution was washed in turn with saturated aqueous bicarbonate and brine. The dried solution was evaporated, and the obtained residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (2:1-3:1, V/V) to give 1-t-butyloxycarbonyl-3-{1-(tetrahydropyran-2-yloxy)ethyl}-2-oxopyrrolidine (18.4 g).

Workup

  1. washthe solution was washed in turn with saturated aqueous bicarbonate and brine
  2. customThe dried solution was evaporated
  3. customthe obtained residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (2:1-3:1, V/V)

Sources & evidence

ORD record
ord-2aebb7bdfde44a40a1c68306b783d67c
Source dataset
uspto-grants-1992_04
Patent number
US05102877

Reaction notes

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