Toluene → HCID 22958910, compound

HRID 2303327Notes

Reaction equation

HRID 2303327 reaction equation
C[N:2]1[CH:7]2[CH:8]([O:10][CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[CH2:9][CH:3]1[CH2:4][C:5](=[O:17])[CH2:6]2.Cl[C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1>CCOCC.[OH-].[Na+]>[CH2:22]([O:21][C:19]([N:2]1[CH:7]2[CH:8]([O:10][CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[CH2:9][CH:3]1[CH2:4][C:5](=[O:17])[CH2:6]2)=[O:20])[CH3:23]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 18461082HCID 18461082, compound

Product 1

HCID 22958910HCID 22958910, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 0.5 g of 8-methyl-6-(tetrahydro-pyran-2-yloxy)-8-aza-bicyclo[3.2.1]octan-3-one, 1 mL of ethyl chloroformate, 25 mg of potassium carbonate, and 10 mL of toluene was heated to reflux overnight. After cooling the mixture was diluted with 500 mL of ether and 50 mL of 3N NaOH and stirred for 2 hours. The organic layer was dried over MgSO4 and concentrated under reduced pressure. Drying under vacuum gave 0.60 g of the ethyl carbamate.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling the mixture
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customDrying under vacuum

Sources & evidence

ORD record
ord-858c11b7c8d540098be0efe8fbd8731e
Source dataset
uspto-grants-2002_08
Patent number
US06432976B1

Reaction notes

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