benzyl 4-((1R,2S)-2-(2-(5-(methylsulfonyl)pyridin-2-yloxy)ethyl)cyclopropyl)piperidine-1-carboxylate → 5-(methylsulfonyl)-2-{2-[(1S,2R)-2-piperidin-4-ylcyclopropyl]ethoxy}pyridine

HRID 1850744Notes

Reaction equation

HRID 1850744 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][C@@H:14]2[CH2:16][C@@H:15]2[CH:17]2[CH2:22][CH2:21][N:20](C(OCC3C=CC=CC=3)=O)[CH2:19][CH2:18]2)=[N:9][CH:10]=1)(=[O:4])=[O:3]>[Pd].C(O)C>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH2:12][CH2:13][C@@H:14]2[CH2:16][C@@H:15]2[CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)=[N:9][CH:10]=1)(=[O:3])=[O:4]

Participants

4

Reactant 1

HCID 70819038benzyl 4-((1R,2S)-2-(2-(5-(methylsulfonyl)pyridin-2-yloxy)ethyl)cyclopropyl)piperidine-1-carboxylate2×

Product 1

HCID 708192275-(methylsulfonyl)-2-{2-[(1S,2R)-2-piperidin-4-ylcyclopropyl]ethoxy}pyridine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl 4-((1R,2S)-2-(2-(5-(methylsulfonyl)pyridin-2-yloxy)ethyl)cyclopropyl)piperidine-1-carboxylate (Intermediate 12; 1.20 g, 2.62 mmol) and palladium on activated carbon (10%, wet, 240 mg) in ethanol (50 mL) were stirred under an atmosphere of hydrogen (1 atm) at RT for 3 h. The mixture was filtered (glass wool filter paper, Whatman 1821 110), and washed with ethanol. The filtrate was concentrated to dryness under reduced pressure to provide the title compound as an off-white solid. 1H NMR (300 MHz, CDCl3) δ 8.72 (dd, J=0.5, 2.5 Hz, 1H), 8.03 (dd, J=2.5, 8.7 Hz, 1H), 6.84 (dd, J=0.6, 8.7 Hz, 1H), 4.48 (t, J=7.2 Hz, 2H), 3.20-3.05 (m, 2H), 3.07 (s, 3H), 2.65-2.50 (m, 2H), 2.20-1.90 (m, 2H), 1.85-1.65 (m, 2H), 1.60-1.45 (m, 1H), 1.45-1.20 (m, 2H), 1.00-0.80 (m, 2H), 0.70-0.60 (m, 2H), −0.13 (q, J=4.2 Hz, 1H). MS (Multimode) m/z 325 [M+H]+.

Workup

  1. filtrationThe mixture was filtered
  2. filtration(glass wool filter paper, Whatman 1821 110)
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-94170d942a3643819e1314057a0345a9
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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