Hydrochloric Acid → HCID 58421715, compound

HRID 406047Notes

Reaction equation

HRID 406047 reaction equation
N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[CH:17]1([OH:23])[CH2:21][CH2:20][CH:19]([OH:22])[CH2:18]1.[F:24][C:25]1[CH:26]=[CH:27][C:28]([N+:32]([O-:34])=[O:33])=[C:29](O)[CH:30]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>C1COCC1.C(Cl)Cl>[F:24][C:25]1[CH:30]=[CH:29][C:28]([N+:32]([O-:34])=[O:33])=[C:27]([CH:26]=1)[O:22][CH:19]1[CH2:20][CH2:21][CH:17]([OH:23])[CH2:18]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 99375-Fluoro-2-nitrophenolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 100165Cyclopentane-1,3-diol

Product 1

HCID 58421715HCID 58421715, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Di-tert-butyl azodicarboxylate was added at 0° C. to a mixture of 1,3-cyclopentandiol (1.02 g), 5-fluoro-2-nitrophenol (0.79 g) and triphenylphosphine (1.97 g) in THF (15.0 ml). After stirring at room temperature over weekend the mixture was treated with 2 M aq. HCl (20.0 ml) and refluxed for 30 min. The reaction mixture was diluted with methylene chloride. The layers were separated. The organic layer was passed through a hydrophobic frit and concentrated in vacuo. The crude was purified by chromatography to yield the desired product.

Workup

  1. temperaturerefluxed for 30 min
  2. customThe layers were separated
  3. concentrationconcentrated in vacuo
  4. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-d7b4eb54906542bcac5bdc80f5cc8688
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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