Acetic Anhydride → HCID 15678881, compound

HRID 258083Notes

Reaction equation

HRID 258083 reaction equation
[CH3:1][N:2]1[C:9]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[CH:7]2[CH2:15][CH:3]1[N:4]([CH3:16])[CH2:5][CH2:6]2.[C:17](OC(=O)C)(=[O:19])[CH3:18].C(=O)(O)[O-].[Na+]>ClCCl>[C:17]([O:14][C:12]1[CH:11]=[CH:10][C:9]2[N:2]([CH3:1])[CH:3]3[CH2:15][CH:7]([CH2:6][CH2:5][N:4]3[CH3:16])[C:8]=2[CH:13]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 15678877HCID 15678877, compound

Product 1

HCID 15678881HCID 15678881, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A catalytic amount, (0.019 g) of N,N-dimethylaminopyridine was added to a deoxygenated solution of 5.8 g of 1,2,3,4,5,6-hexahydro-1,3-dimethyl-2,6-methano-1,3-benzodiazocin-8-ol and 5.4 g of acetic anhydride in 270 ml of dichloromethane. After stirring for 15 minutes, the reaction mixture was treated with a saturated sodium bicarbonate solution. The aqueous layer was separated and extracted with dichloromethane. The combined organic layers were washed with saturated sodium chloride solution, dired over anhydrous magnesium sulfate, filtered and concentrated to an oil (7.1 g). Column chloromatography of a 3.5 g aliquot of the oil (silica gel; elution with triethylamine-methanol-ethyl acetate) afforded 2.2 g of 1,2,3,4,5,6-hexahydro-1,3-dimethyl-2,6-methano-1,3-benzodiazocin-8-ol acetate as a solid.

Workup

  1. customThe aqueous layer was separated
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with saturated sodium chloride solution
  4. filtrationfiltered
  5. concentrationconcentrated to an oil (7.1 g)
  6. washColumn chloromatography of a 3.5 g aliquot of the oil (silica gel; elution with triethylamine-methanol-ethyl acetate)

Sources & evidence

ORD record
ord-b48fcfc5a9b14496a38f8c4a8e9db331
Source dataset
uspto-grants-1993_11
Patent number
US05264575

Reaction notes

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