5-Hexenoic Acid → (3r,3Ar,6r,6ar)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl hex-5-enoate

HRID 1675995Notes

Reaction equation

HRID 1675995 reaction equation
[CH2:1]1[O:5][C@@H:4]2[C@H:6]([OH:9])[CH2:7][O:8][C@@H:3]2[C@@H:2]1[OH:10].[C:11](O)(=[O:17])[CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16].CCN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:11]([O:10][C@@H:2]1[CH2:1][O:5][C@@H:4]2[C@H:6]([OH:9])[CH2:7][O:8][C@H:3]12)(=[O:17])[CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16]

Participants

6

Reactant 3

HCID 153085-Hexenoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 109756241,4:3,6-Dianhydro-D-mannitol

Product 1

HCID 59509518(3r,3Ar,6r,6ar)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl hex-5-enoate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 1,4:3,6-dianhydro-D-mannitol (isommanide) (2.00 g, 13.68 mmol), 5-hexenoic acid (1.60 g, 13.68 mmol) and DMAP (0.17 g, 1.4 mmol) in DCM (50 mL) cooled at 0° C., EDAC (3.1 g, 16.42 mmol) was added. The solution was stirred at room temperature for 6 hrs. The solution was diluted with DCM (30 mL), washed with a solution of NaHPO4 5% (2×40 mL) and brine. The organic layer was dried over sodium sulfate and concentrated under vacuo. The residue was purified by flash chromatography (Biotage SP1, 40+M column, TLC method: n-Hexane/EtOAc −8:2, Rf product: 0.35) yielding the title compound.

Workup

  1. washwashed with a solution of NaHPO4 5% (2×40 mL) and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under vacuo
  4. customThe residue was purified by flash chromatography (Biotage SP1, 40+M column, TLC method: n-Hexane/EtOAc −8:2, Rf product: 0.35)

Sources & evidence

ORD record
ord-8dfa0bc0a97a408db47c58e270018a49
Source dataset
uspto-grants-2011_08
Patent number
US08003811B2

Reaction notes

Loading…