3,4-dihydro-2H-pyran → HCID 10878146, compound

HRID 1969372Notes

Reaction equation

HRID 1969372 reaction equation
[OH:1][CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1.[CH2:9]1[CH2:14][O:13][CH:12]=[CH:11][CH2:10]1.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>ClCCl>[O:13]1[CH2:14][CH2:9][CH2:10][CH2:11][CH:12]1[O:1][CH2:2][C@H:3]1[NH:7][C:6](=[O:8])[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 643511(S)-5-(Hydroxymethyl)-2-pyrrolidinone

Product 1

HCID 10878146HCID 10878146, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (S)-5-(hydroxymethyl)pyrrolidin-2-one (1.0 g, 8.7 mmol, Aldrich) and DHP (1.46 g, 17.4 mmol, Alfa) in 20 mL of dichloromethane was added PPTS (0.437 g, 1.74 mmol, Aldrich) in portions. The reaction mixture was stirred at rt for 4 hrs, and was quenched with 20 mL of saturated NaHCO3 aqueous solution. The resulted mixture was extracted with dichloromethane (25 mL×2). The combined organic phases were dried over Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc) to give the title compound (as a diastereomer mixture) as colorless oil (0.9 g, 52%).

Workup

  1. customwas quenched with 20 mL of saturated NaHCO3 aqueous solution
  2. extractionThe resulted mixture was extracted with dichloromethane (25 mL×2)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by a silica gel column chromatography (EtOAc)

Sources & evidence

ORD record
ord-cdef3cb042db4aa3b5f0cef84189de76
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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