(R)-2-((2-cyano-3-nitrophenoxy)methyl)-N-(pyridin-4-ylmethyl)piperidine-1-carboxamide → (R)-2-((3-amino-2-cyanophenoxy)methyl)-N-(pyridin-4-ylmethyl)piperidine-1-carboxamide

HRID 1483970Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1483970
[C:1]([C:3]1[C:26]([N+:27]([O-])=O)=[CH:25][CH:24]=[CH:23][C:4]=1[O:5][CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)=[O:14])#[N:2]>C1COCC1.C(O)(=O)C.[Fe]>[NH2:27][C:26]1[C:3]([C:1]#[N:2])=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]([NH:15][CH2:16][C:17]1[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=1)=[O:14]

Komponenten

4

Edukt 1

HCID 86714302(R)-2-((2-cyano-3-nitrophenoxy)methyl)-N-(pyridin-4-ylmethyl)piperidine-1-carboxamide

Produkt 1

HCID 86714301(R)-2-((3-amino-2-cyanophenoxy)methyl)-N-(pyridin-4-ylmethyl)piperidine-1-carboxamideAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 23444217Acetic acid tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (R)-2-((2-cyano-3-nitrophenoxy)methyl)-N-(pyridin-4-ylmethyl)piperidine-1-carboxamide (Example 27c, 365 mg, 0.98 mmol) in THF/acetic acid (20 mL, 1:1), was added iron powder (164 mg, 2.94 mmol). The reaction was heated to reflux over 15 min under nitrogen, and stirred at reflux for 30 min. Upon completion, the reaction was cooled to room temperature, concentrated, diluted with ethyl acetate and successively washed a saturated solution of NaHCO3, dried over Na2SO4, filtered, concentrated and flash chromatographed (0-10% methanol in dichloromethane) to provide the desired product (141 mg, 40%). MS=366 (MH+).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux over 15 min under nitrogen
  3. temperatureat reflux for 30 min
  4. concentrationconcentrated
  5. additiondiluted with ethyl acetate
  6. washsuccessively washed a saturated solution of NaHCO3
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customflash chromatographed (0-10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-a01048fd571741228c4c598c8ef824e4
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09420814B2

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