Tetrahydrofuran → HCID 68490057, compound

HRID 1944227Notes

Reaction equation

HRID 1944227 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][C:11]2[CH:15]=[C:16]([O:21][CH2:22]C3C=CC=CC=3)[C:17]([O:19]C)=[CH:18][C:10]=2[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C[O:33]CC1>CO.[Pd]>[CH2:1]([N:8]1[C:14](=[O:33])[CH2:13][CH2:12][CH2:11][C:10]2[CH:18]=[C:17]([OH:19])[C:16]([O:21][CH3:22])=[CH:15][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 68490107HCID 68490107, compound

Product 1

HCID 68490057HCID 68490057, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-benzyl-7-(benzyloxy)-8-methoxy-2,3,4,5-tetrahydro-1H-benzo[c]azepin-1-one (1 mmol) in THF (20 mL) and methanol (20 mL) was treated with 10% Pd/C (40 mg) and stirred under an atmosphere of hydrogen. The reaction was monitored by TLC. Upon completion, the resultant suspension was filtered through celite, washed with ethyl acetate and then evaporated under reduced pressure. The resulting solid was stirred in diethyl ether, filtered and dried under vacuum or purified by flash chromatography (hexane/ethyl acetate) then stirred in diethyl ether, filtered and dried under vacuum.

Workup

  1. filtrationUpon completion, the resultant suspension was filtered through celite
  2. washwashed with ethyl acetate
  3. customevaporated under reduced pressure
  4. stirringThe resulting solid was stirred in diethyl ether
  5. filtrationfiltered
  6. customdried under vacuum
  7. custompurified by flash chromatography (hexane/ethyl acetate)
  8. stirringthen stirred in diethyl ether
  9. filtrationfiltered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-2714eff81b8144bf8d1d85736d7bfe7c
Source dataset
uspto-grants-2013_03
Patent number
US08394825B2

Reaction notes

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