4-Methylmorpholine → (S)-3-(1-(p-Nitrophenoxycarbonyloxy)ethyl)pyridine

HRID 1737102Notes

Reaction equation

HRID 1737102 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][C:9](Cl)=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C@@H:20]([OH:22])[CH3:21])[CH:15]=1.CN1CCOCC1>C(Cl)Cl>[N+:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][C:9]([O:22][C@H:20]([C:16]2[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=2)[CH3:21])=[O:10])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 821294-Nitrophenyl chloroformateHCID 10725338(S)-1-(3-Pyridyl)ethanol

Product 1

HCID 54241400(S)-3-(1-(p-Nitrophenoxycarbonyloxy)ethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A 534 mg (2.65 mmol) sample of p-nitrophenoxycarbonylchloride in methylene chloride was added to a solution of 74 mg (0.606 mmol) of (S)-1-(3-pyridyl)ethanol and 0.080 mL of 4-methylmorpholine in 2 mL of methylene chloride cooled in an ice bath. The mixture was stirred at 0° C. for 3.5 hours. The mixture was diluted with methylene chloride, which was washed with water, dried and concentrated. The crude product was chromatographed on silica gel, eluting with 50% and 90% ethyl acetate in hexane. The solvent was removed and the product dried to afford 0.078 g of the title compound, which was taken directly to the next step.

Workup

  1. temperaturecooled in an ice bath
  2. washwas washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on silica gel
  6. washeluting with 50% and 90% ethyl acetate in hexane
  7. customThe solvent was removed
  8. customthe product dried

Sources & evidence

ORD record
ord-40f3bcf420464826a42f4898d63810e4
Source dataset
uspto-grants-1996_07
Patent number
US05541334

Reaction notes

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