Ethanol → (S)-((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl) 5,6-bis(nitrooxy)hexanoate

HRID 1676000Notes

Reaction equation

[N+:1]([O:4][C@H:5]([CH2:27][O:28][N+:29]([O-:31])=[O:30])[CH2:6][CH2:7][CH2:8][C:9]([O:11][C@@H:12]1[CH2:16][O:15][C@@H:14]2[C@H:17]([O:20]C3CCCCO3)[CH2:18][O:19][C@H:13]12)=[O:10])([O-:3])=[O:2].C(O)C>>[N+:1]([O:4][C@H:5]([CH2:27][O:28][N+:29]([O-:31])=[O:30])[CH2:6][CH2:7][CH2:8][C:9]([O:11][C@@H:12]1[CH2:16][O:15][C@@H:14]2[C@H:17]([OH:20])[CH2:18][O:19][C@H:13]12)=[O:10])([O-:3])=[O:2]

Participants

Reactant 2

HCID 702Ethanol

HCID 58209457(5S)-((3R,3aR,6R,6aR)-6-(tetrahydro-2H-pyran-2-yloxy)-hexahydrofuro[3,2-b]furan-3-yl)5,6-bis(nitrooxy)hexanoate

Product 1

HCID 58209439(S)-((3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl) 5,6-bis(nitrooxy)hexanoate

Conditions

Temperature: 45 °C

Procedure

To a solution of (5S)-((3R,3aR,6R,6aR)-6-(tetrahydro-2H-pyran-2-yloxy)hexahydrofuro[3,2-b]furan-3-yl) 5,6-bis(nitrooxy)hexanoate (2.27 g, 5.04 mmol) in ethanol (40 mL) pyridinium p-toluensulfonate (127 mg, 0.504 mmol) was added The reaction mixture was stirred at 45° C. for 4 hrs. The reaction mixture was filtered, concentrated under reduced pressure. The crude residue was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 10 to 60%), affording the title product as pale yellow oil.

Workup

filtrationThe reaction mixture was filtered
concentrationconcentrated under reduced pressure
customThe crude residue was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 10 to 60%)

Sources & evidence

ORD record: ord-6cb1da875c5b42b4b0d885dc3ca58731
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003811B2

Reaction notes

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