HCID 13519514, compound → HCID 13519531, compound

HRID 371125Notes

Reaction equation

HRID 371125 reaction equation
[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].Cl[C:10]1[CH:15]=[CH:14][C:13]([C:16]23[CH:24]4[CH2:25][CH:21]([CH:22]=[CH:23]4)[CH:20]2[CH2:19][NH:18][CH2:17]3)=[CH:12][CH:11]=1>C(OCC)(=O)C>[C:1]([OH:8])(=[O:7])/[CH:2]=[CH:3]/[C:4]([OH:6])=[O:5].[C:13]1([C:16]23[CH:24]4[CH2:25][CH:21]([CH2:22][CH2:23]4)[CH:20]2[CH2:19][NH:18][CH2:17]3)[CH:12]=[CH:11][CH:10]=[CH:15][CH:14]=1

Participants

3

Reactant 1

HCID 13519514HCID 13519514, compound

Product 1

HCID 13519531HCID 13519531, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 0.49 g portion of 3a-(4-chlorophenyl)-2,3,3a,4,7,7a-hexahydro-4,7-methano-1H-isoindole fumarate was suspended in 30 ml of ethyl acetate, washed twice with 10% sodium bicarbonate solution, dried with brine and 47 mg of 5% palladium on calcium added. The mixture was stirred under one atmosphere of hydrogen for 17 hours, then filtered, washed with 10% sodium bicarbonate, dried and evaporated, giving 0.25 g of the free base of the desired compound as a brown oil.

Workup

  1. washwashed twice with 10% sodium bicarbonate solution
  2. dry with materialdried with brine and 47 mg of 5% palladium on calcium
  3. additionadded
  4. filtrationfiltered
  5. washwashed with 10% sodium bicarbonate
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-2cf9376a49b34ba5b4706649433afd1c
Source dataset
uspto-grants-1985_07
Patent number
US04529736

Reaction notes

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