HCID 68611739, compound → HCID 56951493, compound

HRID 2095308Notes

Reaction equation

HRID 2095308 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C@H:15]2[CH2:17][C@@H:16]2[CH:18]=[CH:19][O:20][CH3:21])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.O=[Pt]=O>[CH2:1]([O:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([C@H:15]2[CH2:17][C@@H:16]2[CH2:18][CH2:19][O:20][CH3:21])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 68611739HCID 68611739, compound

Product 1

HCID 56951493HCID 56951493, compoundYield 99.3%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 6344DichloromethaneSolvent

Procedure

In a 100 mL round-bottom flask, PtO2 (77 mg, 0.34 mmol, 0.05 equiv.) was added under N2 at room temperature to a solution of 3-(benzyloxy)-5-[(1S,2S)-2-(2-methoxyvinyl)cyclopropyl]pyridine (1.90 g, 6.75 mmol) in CH2Cl2 (18 mL). A H2 balloon was attached, and the atmosphere was exchanged three times. The reaction mixture was stirred at room temperature for 6 h, after which time TLC analysis indicated that the starting material had disappeared completely. The catalyst was filtered off and washed with CH2Cl2 (2×5 mL). The combined filtrates were concentrated in vacuo to yield crude 3-(benzyloxy)-5-[(1S,2R)-2-(2-methoxyethyl)cyclopropyl]pyridine (1.90 g) as a yellowish oil. LC-MS (ESI) m/z 284 (M+H+).

Workup

  1. filtrationThe catalyst was filtered off
  2. washwashed with CH2Cl2 (2×5 mL)
  3. concentrationThe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-23956fed6fb447f688185ea8f9531185
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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