Phenylmethyl 9-(2-ethoxy-2-oxoethylidene)-3-azaspiro[5.5]undec-7-ene-3-carboxylate → HCID 22975760, compound

HRID 2120954Notes

Reaction equation

HRID 2120954 reaction equation
[CH2:1]([O:3][C:4]([CH:6]=[C:7]1[CH2:27][CH2:26][C:10]2([CH2:15][CH2:14][N:13](C(OCC3C=CC=CC=3)=O)[CH2:12][CH2:11]2)[CH:9]=[CH:8]1)=[O:5])[CH3:2].[H][H]>C(O)C>[CH2:15]1[C:10]2([CH2:26][CH2:27][CH:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:8][CH2:9]2)[CH2:11][CH2:12][NH:13][CH2:14]1

Participants

4

Reactant 2

HCID 54192656Phenylmethyl 9-(2-ethoxy-2-oxoethylidene)-3-azaspiro[5.5]undec-7-ene-3-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 22975760HCID 22975760, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9.6 g (26.0 mmol) of the protected Spiro compound from Step B were dissolved in 400 ml ethanol, and the solution was filled into a hydrogenation vessel followed by 2 g Pd(II) hydroxide on charcoal. The reaction was carried out at 40° C. and 1 atm hydrogen, and it was complete after about 40 hours. The catalyst was removed by filtration through silica gel, and the filtrate was concentrated under reduced pressure. The remaining oil was treated with dry ether, filtered, and the filtrate was acidified with ethereal hydrochloric acid. The hydrochloride of the title compound was collected by filtration, washed two times with ether, dissolved in water, and the solution was made alkaline with 2 N aqueous sodium hydroxide solution. After extraction with dichloromethane the organic layer was dried over sodium sulfate and concentrated in vacuo.

Workup

  1. additionthe solution was filled into a hydrogenation vessel
  2. customwas carried out at 40° C.
  3. customThe catalyst was removed by filtration through silica gel
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionThe remaining oil was treated with dry ether
  6. filtrationfiltered
  7. filtrationThe hydrochloride of the title compound was collected by filtration
  8. washwashed two times with ether
  9. dissolutiondissolved in water
  10. extractionAfter extraction with dichloromethane the organic layer
  11. dry with materialwas dried over sodium sulfate
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8dfaabf8409842ddbbadc148e5a9fcb3
Source dataset
uspto-grants-2004_02
Patent number
US06693109B2

Reaction notes

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