Tert-butyl 4-(1H-pyrrolo[2,3-B]pyridin-3-YL)-5,6-dihydropyridine-1(2H)-carboxylate → tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylate

HRID 1370041Notes

Reaction equation

HRID 1370041 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.O=[Pt]=O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 45790246Tert-butyl 4-(1H-pyrrolo[2,3-B]pyridin-3-YL)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 49758876tert-butyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

4-(1H-Pyrrolo[2,3-b]pyridin-3-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (1 g, 3.3 mmol) in EtOH (25 mL) containing PtO2 (250 mg) was placed on a Parr hydrogenator at 60 psi H2. After 18 h the mixture was filtered through celite and evaporated to give 0.96 g (97%) of a white solid. TLC (silica, 50% EtOAc/hexanes): Rf=0.5. MS (electrospray): exact mass calculated for C17H23N3O22, 301.18; m/z found, 302.2 [M++H]. 1H NMR (CDCl3, 400 MHz) 10.95 (br s, 1H), 8.26 (dd, J=3.33 Hz, 1.37 Hz, 1H), 7.96 (dd, J=6.26 Hz, 1.57 Hz, 1H), 7.11 (s, 1H), 7.05 (dd, J=4.89 Hz, 3.13 Hz, 1H), 4.22 (br s, 2H), 3.00-2.79 (m, 3H), 1.99 (d, J=13.89 Hz, 2H), 1.74-1.60 (m, 2H), 1.47 (s, 9H).

Workup

  1. filtrationAfter 18 h the mixture was filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-9de5a84468e94e3287b62d0364c9e95e
Source dataset
uspto-grants-2003_06
Patent number
US06579896B2

Reaction notes

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