(3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-nitrophenyl carbonate → 3,3-dimethyl-5,6-bis(nitrooxy)hexyl (3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl carbonate

HRID 1676006Notes

Reaction equation

HRID 1676006 reaction equation
[N+:1]([O-:17])([O:3][CH2:4][CH:5]([O:13][N+:14]([O-:16])=[O:15])[CH2:6][C:7]([CH3:12])([CH3:11])[CH2:8][CH2:9][OH:10])=[O:2].[C:18](=O)([O:29]C1C=CC([N+]([O-])=O)=CC=1)[O:19][C@@H:20]1[CH2:24][O:23][C@@H:22]2[C@H:25]([OH:28])[CH2:26][O:27][C@H:21]12>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:18](=[O:29])([O:19][C@@H:20]1[CH2:24][O:23][C@@H:22]2[C@H:25]([OH:28])[CH2:26][O:27][C@H:21]12)[O:10][CH2:9][CH2:8][C:7]([CH3:12])([CH3:11])[CH2:6][CH:5]([O:13][N+:14]([O-:16])=[O:15])[CH2:4][O:3][N+:1]([O-:17])=[O:2]

Participants

5

Reactant 2

HCID 58209393(3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-nitrophenyl carbonate2×HCID 597787456-Hydroxy-4,4-dimethylhexane-1,2-diyl dinitrate

Product 1

HCID 441803883,3-dimethyl-5,6-bis(nitrooxy)hexyl (3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 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 (0.962 g, 3.10 mmol) in DCM (40 ml), (prepared as described in EXAMPLE 7, Step C), 6-hydroxy-4,4-dimethylhexane-1,2-diyl dinitrate (0.780, 3.10 mmol) and 4-dimethylaminopyridine (0.379 g, 3.10 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 (2×30 ml) and brine (1×30 ml). The organic layer was dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 20 to 80%), affording the title compound.

Workup

  1. washwashed with a 5% solution of sodium dihydrogen phosphate (2×30 ml) and brine (1×30 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 20 to 80%)

Sources & evidence

ORD record
ord-171f08bcbc3849d18f2f3601871525ce
Source dataset
uspto-grants-2011_08
Patent number
US08003811B2

Reaction notes

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