4-Methylmorpholine → HCID 58822071, compound

HRID 459533Notes

Reaction equation

HRID 459533 reaction equation
[N:1]([C@@H:4]1[C@@H:9]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][CH2:7][C@@H:6]([C:18](O)=[O:19])[CH2:5]1)=[N+:2]=[N-:3].ClC(OCC(C)C)=O.CN1CCOCC1>C(COC)OC>[N:1]([C@@H:4]1[C@@H:9]([NH:10][C:11]([O:13][C:14]([CH3:15])([CH3:16])[CH3:17])=[O:12])[CH2:8][CH2:7][C@@H:6]([CH2:18][OH:19])[CH2:5]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 58822143HCID 58822143, compound

Product 1

HCID 58822071HCID 58822071, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

(1R,3S,4S)-3-Azido-4-(N-tert-butoxycarbonylamino)cyclohexane-1-carboxylic acid (1.86 g) was dissolved in dimethoxyethane (20 ml), and to the solution isobutyl chloroformate (1.02 ml) and N-methylmorpholine (860 mg) were added at −15° C. The mixture was stirred for 10 minutes at the same temperature. The hydrochloride of N-morpholine deposited was separated by filtration, and an aqueous solution (4 ml) of sodium borohydride (370 mg) was added to the filtrate to stir the mixture for 10 minutes. After water was added, and the solvent was distilled off under reduced pressure, the residue was extracted with dichloromethane and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1) to obtain the title compound (1.35 g) as a colorless oil.

Workup

  1. customThe hydrochloride of N-morpholine deposited was separated by filtration
  2. additionan aqueous solution (4 ml) of sodium borohydride (370 mg) was added to the filtrate
  3. stirringto stir the mixture for 10 minutes
  4. additionAfter water was added
  5. distillationthe solvent was distilled off under reduced pressure
  6. extractionthe residue was extracted with dichloromethane
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-18c9a2374d40448599e49201f35ae6c8
Source dataset
uspto-grants-2007_03
Patent number
US07192968B2

Reaction notes

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