Triethylamine → (3R,3aR,6R,6aR)-4-nitrooxy-piperidine-1-carboxylic acid 6-(4-nitro-phenoxycarbonyloxy)-hexahydro-furo[3,2-b]furan-3-yl ester

HRID 1643402Notes

Reaction equation

HRID 1643402 reaction equation
[N+:1]([O:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C@@H:14]2[CH2:18][O:17][C@@H:16]3[C@H:19]([OH:22])[CH2:20][O:21][C@H:15]23)=[O:12])[CH2:7][CH2:6]1)([O-:3])=[O:2].CCN(CC)CC.Cl[C:31]([O:33][C:34]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][CH:35]=1)=[O:32]>C1COCC1>[N+:40]([C:37]1[CH:38]=[CH:39][C:34]([O:33][C:31]([O:22][C@H:19]2[C@H:16]3[O:17][CH2:18][C@@H:14]([O:13][C:11]([N:8]4[CH2:7][CH2:6][CH:5]([O:4][N+:1]([O-:3])=[O:2])[CH2:10][CH2:9]4)=[O:12])[C@H:15]3[O:21][CH2:20]2)=[O:32])=[CH:35][CH:36]=1)([O-:42])=[O:41]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 44180277(3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-(nitrooxy)piperidine-1-carboxylate

Product 1

HCID 59178196(3R,3aR,6R,6aR)-4-nitrooxy-piperidine-1-carboxylic acid 6-(4-nitro-phenoxycarbonyloxy)-hexahydro-furo[3,2-b]furan-3-yl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3R,3aR,6R,6aR)-6-hydroxyhexahydrofuro[3,2-b]furan-3-yl 4-(nitrooxy)piperidine-1-carboxylate (0.47 g, 1.48 mmol) and Et3N (0.45 g, 4.44 mmol) in THF (25 mL) was added 4-Nitrophenyl chloroformate (0.30 g, 1.48 mmol) as solid. After stirring at rt over night, the mixture was concentrated. The residue was diluted with EtOAc and washed with NaH2PO4 5%. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (Biotage SP1; column SNAP 50; 60% EtOAc in n-hexane), affording the title product as a white solid. 1H-NMR (300 MHz, CDCl3); δ 8.33-8.29 (2H, m), 7.45-7.40 (2H, m), 5.22-5.07 (3H, m), 4.88-4.80 (1H, m), 4.79-4.71 (1H, m), 4.20-3.71 (6H, m), 3.60-3.30 (2H, m), 2.12-1.98 (2H, m), 1.88-1.73 (2H, m).

Workup

  1. concentrationthe mixture was concentrated
  2. additionThe residue was diluted with EtOAc
  3. washwashed with NaH2PO4 5%
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (Biotage SP1; column SNAP 50; 60% EtOAc in n-hexane)

Sources & evidence

ORD record
ord-25e80e5bcb2f426782961f5295f7889f
Source dataset
uspto-grants-2012_02
Patent number
US08119806B2

Reaction notes

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