((R)-1-Phenylethyl)-(S)-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-ylamine → (S)-2,7,8,9-Tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-ylamine

HRID 25333Notes

Reaction equation

HRID 25333 reaction equation
C1([C@H]([NH:9][C@@H:10]2[C:19]3[CH2:18][O:17][CH:16]=[CH:15][C:14]4=[CH:20][NH:21][CH:22]=[C:12]([C:13]=34)[CH2:11]2)C)C=CC=CC=1.[H][H]>O1CCCC1.[OH-].[Pd+2].[OH-]>[CH:22]1[NH:21][CH:20]=[C:14]2[CH:15]=[CH:16][O:17][CH2:18][C:19]3[C@@H:10]([NH2:9])[CH2:11][C:12]=1[C:13]2=3

Participants

5

Reactant 2

HCID 69738166((R)-1-Phenylethyl)-(S)-2,7,8,9-tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-ylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 69738048(S)-2,7,8,9-Tetrahydro-6-oxa-2-azabenzo[cd]azulen-8-ylamineYield 86%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Compound (29) 609 mg was dissolved in tetrahydrofuran 20 ml. 20% Palladium(II)hydroxide 200 mg was added. A mixture was stirred in a hydrogen atomosphere for 22 h. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The residue obtained was chromatographed on aluminum oxide in chloroform to give the titled compound (31) as pale brown crystals, 337 mg. Yield 86%. Furthermore, this was recrystallized from methanol-isopropanol to give the titled compound (31) as pale brown crystals, m.p. 202-203° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue obtained
  4. customwas chromatographed on aluminum oxide in chloroform

Sources & evidence

ORD record
ord-bef4abc45ff44e46be142e66008f7e76
Source dataset
uspto-grants-2005_02
Patent number
US06858640B2

Reaction notes

Loading…