tert-Butyl 4-(5-nitro-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate → tert-butyl 4-(5-amino-1H-indol-3-yl)piperidine-1-carboxylate

HRID 552943Notes

Reaction equation

HRID 552943 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[C:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH:14]=1)([O-])=O>N.CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]1

Participants

5

Reactant 1

HCID 54262828tert-Butyl 4-(5-nitro-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 53986362tert-butyl 4-(5-amino-1H-indol-3-yl)piperidine-1-carboxylateYield 100.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

A solution of compound 85 (0.5 g, 1.456 mmol) in 2 M NH3 in methanol (15 mL) was treated with Pd—C (0.05 g) and purged with hydrogen gas. The reaction was stirred under hydrogen atm. for overnight. The solution was filtered through a celite bed and washed with methanol: CH2Cl2 (1:1, 2 20 mL). The combined organic layer was evaporated to obtain compound 86 (0.46 g, quantitative) as a solid. mp 205-207° C.; 1H NMR (DMSO-d6) δ 1.41-1.53 (m, 11H), 1.87-1.91 (m, 2H), 2.73-2.85 (m, 3H), 4.03-4.07 (m, 2H), 4.43 (s, 2H), 6.45 (dd, 1H, J=1.8, 8.4 Hz), 6.69 (d, 1H, J=1.5 Hz), 6.90 (d, 1H, J=2.4 Hz), 7.01 (d, 1H, J=8.4 Hz), 10.28 (s, 1H); ESI-MS m/z (%): 338 (M.Na+, 23), 316 (MH+, 11), 216 (100).

Workup

  1. custompurged with hydrogen gas
  2. filtrationThe solution was filtered through a celite bed
  3. washwashed with methanol: CH2Cl2 (1:1, 2 20 mL)
  4. customThe combined organic layer was evaporated

Sources & evidence

ORD record
ord-b6c8f90d64504bc4b8899ba7335c10e1
Source dataset
uspto-grants-2011_05
Patent number
US07951940B2

Reaction notes

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