6-Chloro-1-hexanol → (3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 6-chlorohexyl carbonate

HRID 1676014Notes

Reaction equation

HRID 1676014 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][OH:8].[C:9](=O)([O:20]C1C=CC([N+]([O-])=O)=CC=1)[O:10][C@@H:11]1[CH2:15][O:14][C@@H:13]2[C@H:16]([OH:19])[CH2:17][O:18][C@H:12]12>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:9](=[O:20])([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Cl:1])[O:10][C@@H:11]1[CH2:15][O:14][C@@H:13]2[C@H:16]([OH:19])[CH2:17][O:18][C@H:12]12

Participants

5

Reactant 2

HCID 748286-Chloro-1-hexanolHCID 58209393(3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-nitrophenyl carbonate2×

Product 1

HCID 59509509(3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 6-chlorohexyl carbonate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-nitrophenyl carbonate (1.13 g, 3.63 mmol) in DCM (15 ml), (prepared as described in EXAMPLE 7, Step C), 6-chlorohexanol (596 mg, 4.36 mmol) and 4-dimethylaminopyridine (89 mg, 0.73 mmol) were added and the mixture was stirred at room temperature for 18 hrs. Then the mixture was diluted with DCM and washed with a 5% solution of sodium dihydrogen phosphate (20 ml). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 12 to 80%), affording the title compound as colorless oil.

Workup

  1. washwashed with a 5% solution of sodium dihydrogen phosphate (20 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 12 to 80%)

Sources & evidence

ORD record
ord-ce6e0a7cb6a84034b4b1b37ffda40aad
Source dataset
uspto-grants-2011_08
Patent number
US08003811B2

Reaction notes

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