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

HRID 1643408Notes

Reaction equation

O1CCCCC1[O:7][C@H:8]1[C@H:12]2[O:13][CH2:14][C@@H:15]([O:16][C:17](=[O:31])[CH2:18][CH2:19][CH2:20][C@H:21]([O:27][N+:28]([O-:30])=[O:29])[CH2:22][O:23][N+:24]([O-:26])=[O:25])[C@H:11]2[O:10][CH2:9]1.C(O)C>>[OH:7][C@H:8]1[C@H:12]2[O:13][CH2:14][C@@H:15]([O:16][C:17](=[O:31])[CH2:18][CH2:19][CH2:20][C@H:21]([O:27][N+:28]([O-:30])=[O:29])[CH2:22][O:23][N+:24]([O-:26])=[O:25])[C@H:11]2[O:10][CH2:9]1

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. 1H-NMR (300 MHz, CDCl3); δ 5.30 (1H, dd), 5.16 (1H, q), 4.77 (1H, d), 4.71 (1H, t), 4.50 (2H, m), 4.26 (1H, m), 4.12 (1H, dd), 3.94 (1H, dd), 3.85 (1H, dd), 3.58 (1H, dd), 2.61 (1H, d), 2.47 (2H, m), 1.83 (4H, m).

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-8d915951fe2844358cefd25d336ddab3
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119806B2

Reaction notes

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