Triethylamine → (3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-(nitrooxy)piperidine-1-carboxylate
Reaction equation
Cl.[N+:2]([O-:11])([O:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)=[O:3].C(N(CC)CC)C.[C:19](=O)([O:30]C1C=CC([N+]([O-])=O)=CC=1)[O:20][C@@H:21]1[CH2:25][O:24][C@@H:23]2[C@H:26]([OH:29])[CH2:27][O:28][C@H:22]12>CN(C)C1C=CN=CC=1.C(Cl)Cl>[N+:2]([O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:19]([O:20][C@@H:21]2[CH2:25][O:24][C@@H:23]3[C@H:26]([OH:29])[CH2:27][O:28][C@H:22]23)=[O:30])[CH2:7][CH2:6]1)([O-:11])=[O:3]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of piperidin-4-yl nitrate hydrochloride (0.620 g, 3.40 mmol), triethylamine (0.567 ml, 4.07 mmol) and 4-dimethylaminopyridine (0.083 g, 0.680 mmol) in DCM (23 ml), (3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-nitrophenyl carbonate (1.06 g, 3.40 mmol) was added; 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, concentrated and purified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 30 to 100%), affording the title compound as a yellow oil.
Workup
- washwashed with a 5% solution of sodium dihydrogen phosphate (2×30 ml) and brine (1×30 ml)
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- custompurified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 30 to 100%)
Sources & evidence
- ORD record
- ord-dbe84d872d3944f2a3379e7d5ab76eef
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08003811B2
Reaction notes
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