HCID 67779826, compound → HCID 18940613, compound

HRID 356210Notes

Reaction equation

HRID 356210 reaction equation
[C:1]1([CH:7]=[CH:8][CH2:9][N:10]2[C:16](=[O:17])[CH:15]3[CH2:18][CH2:19][CH2:20][CH:14]3[NH:13][C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]2=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.[C].[Pd]>[C:1]1([CH2:7][CH2:8][CH2:9][N:10]2[C:16](=[O:17])[CH:15]3[CH2:18][CH2:19][CH2:20][CH:14]3[NH:13][C:12]3[CH:21]=[CH:22][CH:23]=[CH:24][C:11]2=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 67779826HCID 67779826, compound

Product 1

HCID 18940613HCID 18940613, compoundYield 1,097.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of 9-(3-phenyl-2-propen-1-yl)-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (1.0 g, 3.1 mmol) in methanol (10 mL) was added 10% palladium-carbon (hydrous) (0.1 g). The mixture was stirred for 30 minutes at room temperature under hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure. To the concentrate were added ethyl acetate and hexane. Insoluble material was filtered off, and the filtrate was concentrated, which was subjected to a silica-gel column chromatography (hexane-ethyl acetate 10:1) to afford the desired product (10.90 g, 90%) as an oily product.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the concentrate were added ethyl acetate and hexane
  4. filtrationInsoluble material was filtered off
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b4150ff65f54435bbfeb3d44ad7dbdba
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Reaction notes

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