Nitrogen → Ethyl 3-amino-6-(1,4-dioxaspiro[4.5]dec-8-yl)pyridine-2-carboxylate

HRID 1948047Notes

Reaction equation

HRID 1948047 reaction equation
[NH2:1][C:2]1[C:3]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:4][C:5]([C:8]2[CH2:17][CH2:16][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:10][CH:9]=2)=[CH:6][CH:7]=1.N#N>CCO.[Pd]>[NH2:1][C:2]1[C:3]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:4][C:5]([CH:8]2[CH2:9][CH2:10][C:11]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:16][CH2:17]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 947NitrogenHCID 67255067Ethyl 3-amino-6-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine-2-carboxylate2×

Product 1

HCID 67253957Ethyl 3-amino-6-(1,4-dioxaspiro[4.5]dec-8-yl)pyridine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Pd/C (345 mg, 0.0812 mmol) was added to a solution of ethyl 3-amino-6-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)pyridine-2-carboxylate (Compound 232F, 247 mg, 0.812 mmol) in EtOH (5.0 mL). The flask containing this mixture was subjected to 3 cycles of evacuation and N2 purging. After the 4th evacuation the flask was purged with H2 and allowed to stir for 24 hours. The reaction mixture was filtered through celite, the filter cake was washed with MeOH and DCM. The combined filtrate was concentrated to 228 mg of a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 1.30 (t, J=7.07 Hz, 3H), 1.59 (dd, J=12.51, 5.43 Hz, 2H), 1.63-1.70 (m, 2H), 1.70-1.79 (m, 4H), 2.59 (tt, J=11.15, 3.51 Hz, 1H), 3.87 (s, 4H), 4.28 (q, J=7.07 Hz, 2H), 6.50 (s, 2H), 7.17 (s, 2H). MS (ES+): m/z=306.91 (100) [M+1]. HPLC: tR=3.19 min (ZQ3, polar—5 min).

Workup

  1. additionThe flask containing this mixture
  2. customAfter the 4th evacuation the flask was purged with H2
  3. filtrationThe reaction mixture was filtered through celite
  4. washthe filter cake was washed with MeOH and DCM
  5. concentrationThe combined filtrate was concentrated to 228 mg of a yellow solid
  6. custom5 min

Sources & evidence

ORD record
ord-37364a5fbf10494286d195b5974ea396
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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