Acetic Acid → tert-Butyl [1-(3-amino-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)-3-methylpiperidin-3-yl]carbamate

HRID 1499546Notes

Reaction equation

HRID 1499546 reaction equation
[CH3:1][C:2]1([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[C:13]([N+:14]([O-])=O)=[CH:12][N:11]=[C:10]3[CH2:17][CH2:18][CH2:19][C:9]=23)[CH2:3]1.CC(O)=O>CCOC(C)=O.[Fe]>[NH2:14][C:13]1[C:8]([N:4]2[CH2:5][CH2:6][CH2:7][C:2]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:1])[CH2:3]2)=[C:9]2[CH2:19][CH2:18][CH2:17][C:10]2=[N:11][CH:12]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 86726776tert-Butyl [3-methyl-1-(3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate

Product 1

HCID 86726777tert-Butyl [1-(3-amino-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)-3-methylpiperidin-3-yl]carbamateYield 90%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl [3-methyl-1-(3-nitro-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl)piperidin-3-yl]carbamate (100.0 mg, 0.27 mmol), AcOH (1.44 mL) and iron powder (222 mg, 3.98 mmol) was stirred at room temperature for 1 h. The reaction mixture was diluted with EtOAc, filtered through a short silica gel plug. The residue was rinsed with fresh EtOAc and filtered. The filtrate was concentrated under reduced pressure, diluted with EtOAc and neutralized with Na2CO3 solution. After vacuum filtration to remove insoluble impurities, the aqueous layer was extracted with EtOAc three times. The combined organic layers were dried, filtered and concentrated under reduced pressure to give the sub-title compound as off-white powder (80 mg, 90%). LCMS calc. for C19H31N4O2 (M+H)+: m/z=347.2. Found: 347.2.

Workup

  1. filtrationfiltered through a short silica gel plug
  2. washThe residue was rinsed with fresh EtOAc
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. additiondiluted with EtOAc and neutralized with Na2CO3 solution
  6. filtrationAfter vacuum filtration
  7. customto remove insoluble impurities
  8. extractionthe aqueous layer was extracted with EtOAc three times
  9. customThe combined organic layers were dried
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-e11641ac2acc441583710c437a8f2a0c
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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