3,4-dihydro-2H-pyran → HCID 11381597, compound

HRID 1006156Notes

Reaction equation

HRID 1006156 reaction equation
[NH:1]1[CH2:7][CH2:6][CH2:5][C@H:2]1[CH2:3][OH:4].C(=O)([O-])O.[Na+].Cl[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15].[O:24]1[CH:29]=[CH:28][CH2:27][CH2:26][CH2:25]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CN(C)C=O>[CH2:17]([O:16][C:14]([N:1]1[CH2:7][CH2:6][CH2:5][C@H:2]1[CH2:3][O:4][CH:25]1[CH2:26][CH2:27][CH2:28][CH2:29][O:24]1)=[O:15])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 5

HCID 80803,4-dihydro-2H-pyranHCID 10387Benzyl chloroformateHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 516892Sodium BicarbonateHCID 640091L-Prolinol

Product 1

HCID 11381597HCID 11381597, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of L-prolinol (1.00 g, 4.94 mmol) in N,N-dimethylformamide (5 mL) was cooled to 0° C. and treated with sodium hydrogencarbonate (831 mg, 9.87 mmol) and benzyl chloroformate (843 mg, 4.94 mmol). After removal of the ice bath the reaction mixture was stirred 1 h at r.t. then poured onto ice and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4) and evaporated. The residue was taken up in dichloromethane (5 mL), treated with 3,4-dihydro-2H-pyran (1.25 g, 14.8 mmol) and pyridinium toluene-4-sulfonate (1.37 g, 5.43 mmol) and stirred for 48 h at r.t., then evaporated. The residue was partitioned between ethyl acetate and water, the organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, hexane/ethyl acetate 3:1) yielded the title compound (451 mg, 29%). Colourless liquid, ISP-MS: m/e=320.4 ([M+H]+).

Workup

  1. customAfter removal of the ice bath the reaction mixture
  2. additionthen poured onto ice
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. stirringstirred for 48 h at r.t.
  8. customevaporated
  9. customThe residue was partitioned between ethyl acetate and water
  10. washthe organic layer was washed with brine
  11. dry with materialdried (MgSO4)
  12. customevaporated

Sources & evidence

ORD record
ord-15c735ae3384484791963c027fb09d1c
Source dataset
uspto-grants-2004_09
Patent number
US06787558B2

Reaction notes

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