HCID 54110954, compound → HCID 53863065, compound

HRID 268178Notes

Reaction equation

HRID 268178 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[N:18]([CH3:19])[C:17](=[O:20])[CH:16]3[CH2:21][CH2:22][CH2:23][N:15]3[CH2:14][C:13]=2[CH:24]=1)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[N:18]([CH3:19])[C:17](=[O:20])[CH:16]3[CH2:21][CH2:22][CH2:23][N:15]3[CH2:14][C:13]=2[CH:24]=1

Participants

5

Reactant 2

HCID 54110954HCID 54110954, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 53863065HCID 53863065, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 6.44 g. of 7-benzyloxy-1,2,3,5,10,11a- hexahydro-10-methyl-11H-pyrrolo[2,1-c] [1,4]benzodiazepin-11- one, 200 ml. of ethanol and 1.0 g. of 10% palladium-on-carbon catalyst is shaken in a Parr hydrogenator under about 3 atmospheric of hydrogen pressure until the theoretical amount of hydrogen is absorbed. The catalyst is filtered off and the mother liquor is concentrated to remove the solvent. The residue is purified by partition chromatography on a diatomaceous earth column using a heptane/methyl cellosolve solvent system to yield pure 1,2,3,5,10,11a-hexahydro-7-hydroxy- 10-methyl-11H-pyrrolo[2,1-c] [1,4]benzodiazepin-11-one.

Workup

  1. additionA mixture of 6.44 g
  2. customis absorbed
  3. filtrationThe catalyst is filtered off
  4. concentrationthe mother liquor is concentrated
  5. customto remove the solvent
  6. customThe residue is purified
  7. customby partition chromatography on a diatomaceous earth column

Sources & evidence

ORD record
ord-38834a805c084876aa43b7de5190402d
Source dataset
uspto-grants-1976_03
Patent number
US03947408

Reaction notes

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