Triethylamine → (3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-(nitrooxy)piperidine-1-carboxylate

HRID 1643401Notes

Reaction equation

HRID 1643401 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

HCID 8471TriethylamineHCID 58209393(3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-nitrophenyl carbonateHCID 66753481Piperidin-4-yl nitrate hydrochloride

Product 1

HCID 44180277(3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-(nitrooxy)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

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

  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. custompurified by flash chromatography (Biotage SP1, EtOAc/n-hexane from 30 to 100%)

Sources & evidence

ORD record
ord-e73b49a4366545b5b75f738fb840275e
Source dataset
uspto-grants-2012_02
Patent number
US08119806B2

Reaction notes

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