Pyridine → HCID 19065976, compound

HRID 964359Notes

Reaction equation

HRID 964359 reaction equation
[OH:1][CH:2]1[CH2:9][CH2:8][C:5]2([O:7][CH2:6]2)[CH:4]([C:10]2([CH3:18])[CH:12]([CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[O:11]2)[CH:3]1[O:19][CH3:20].[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl[C:28](OC1C=CC([N+]([O-])=O)=CC=1)=[O:29].N1CCCCC1>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)C>[CH3:20][O:19][CH:3]1[CH:2]([O:1][C:28]([N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:29])[CH2:9][CH2:8][C:5]2([O:7][CH2:6]2)[CH:4]1[C:10]1([CH3:18])[CH:12]([CH2:13][CH:14]=[C:15]([CH3:17])[CH3:16])[O:11]1

Participants

8

Reactant 4

HCID 1049PyridineHCID 8082PiperidineHCID 821294-Nitrophenyl chloroformateHCID 2190894-(1,5-Dimethyl-1,2-epoxy-4-hexenyl)-5-methoxy-1-oxaspiro(2.5)octan-6-ol

Product 1

HCID 19065976HCID 19065976, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 6-hydroxy-5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2,5]octane (26 mg), pyridine (44 μl), and 4-dimethylaminopyridine (2 mg) in dichloromethane (0.8 ml) was added dropwise 4-nitrophenyl chloroformate (20 mg) at ambient temperature. After stirring for 2 hours, piperidine (40 μl) was added in one portion. The solution was stirred overnight at ambient temperature and then diluted with diethyl ether (20 ml). The mixture was washed with brine, aqueous saturated sodium bicarbonate solution, and brine successively. The mixture was dried and evaporated under reduced pressure to give a crude oil, which was purified by preparative thin layer chromatography to yield 5-methoxy-4-[2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-6-piperidinocarbonyloxy-1-oxaspiro[2,5]octane (34.3 mg).

Workup

  1. stirringThe solution was stirred overnight at ambient temperature
  2. washThe mixture was washed with brine, aqueous saturated sodium bicarbonate solution, and brine successively
  3. customThe mixture was dried
  4. customevaporated under reduced pressure
  5. customto give a crude oil, which
  6. customwas purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-25bf80ccdcbb4f4183e69f54b17ade53
Source dataset
uspto-grants-1998_06
Patent number
US05767293

Reaction notes

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