Acetic Anhydride → HCID 23358127, compound

HRID 1721397Notes

Reaction equation

HRID 1721397 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[C:16]([OH:21])=[C:17]([OH:20])[CH:18]=[CH:19][C:11]=2[CH2:10]1.C([O-])(=O)C.[Na+]>O>[C:1]([NH:8][CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[C:16]([OH:21])=[C:17]([OH:20])[CH:18]=[CH:19][C:11]=2[CH2:10]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 22415046HCID 22415046, compound

Product 1

HCID 23358127HCID 23358127, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Acetic anhydride is added to a mixture of 6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene-1,2-diol Cannon, J. G., et al., J. Med. Chem., 27, 922(1984)! in water containing sodium acetate. The mixture is chilled and stirred in ice for 4 hours followed by filtration to give N-acetyl-6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene-1,2-diol. Benzyl bromide, powdered potassium carbonate and acetone is added to the isolated N-acetyl-6-amino-6,7,8,9-tetrahydro-5H-benzocycloheptene-1,2-diol and the mixture is stirred for 18 hours. The reaction mixture is poured into water, extracted and concentrated in vacuo to give N-acetyl-6-amino-1,2-dibenzyloxy-6,7,8,9-tetrahydro-5H-benzocycloheptene. Hydrolysis with ethanolic sodium hydroxide gives 6-amino-1,2-dibenzyloxy-6,7,8,9-tetrahydro-5H-benzocycloheptene.

Workup

  1. temperatureThe mixture is chilled
  2. filtrationfollowed by filtration

Sources & evidence

ORD record
ord-87ac166236ef4c05affefbb85931cdc0
Source dataset
uspto-grants-1996_04
Patent number
US05510376

Reaction notes

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