Methanol → HCID 22229146, compound

HRID 1744401Notes

Reaction equation

HRID 1744401 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]=[C:7]1[CH2:12][CH2:11][CH2:10][NH:9][C:8]1=[O:13].CO>[Ir].ClCCl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][NH:9][C:8]1=[O:13]

Participants

5

Reactant 2

HCID 887MethanolHCID 69554317HCID 69554317, compound

Product 1

HCID 22229146HCID 22229146, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23924IridiumCatalystHCID 6344DichloromethaneSolvent

Procedure

This example describes the preparation of I where n=2 and R1=2-furanyl. In a nitrogen-filled glove box, a Fisher-Porter tube was charged with iridium catalyst prepared as in Example 1 (10 mg, 0.012 mmol) and 3-(2-furanylmethylidene)-2-piperidone (250 mg, 1.4 mmol). Methanol (3 mL) and dichloromethane (3 mL) were added and the system was flushed 4 times with hydrogen and pressured to 60 psi (0.5 MPa) H2. After 18 h the reaction mixture was filtered through a short pad of silica. The solvent was removed at reduced pressure to afford 3-(2-furanylmethyl)-2-piperidone (230 mg, 92%) as a white crystalline solid. Chiral HPLC analysis (Chiralpak AD, 85% heptane, 15% ethanol, 30° C.) indicated that conversion was 100% and the enantiomeric excess was 95%. 13C NMR: δ 21.55, 26.12, 29.99, 40.91, 42.57, 106.80, 110.39, 141.38, 153.99, 174.20; 1H NMR: δ 1.49 (m, 1H), 1.68 (m, 1H), 1.75-1.91 (m, 2H), 2.62 (m, 1H), 2.82 (m, 1H), 3.29 (m, 3H), 6.06 (m, 1H), 6.29 (m, 1H), 7.29 (m, 1H), 7.34 (br s, 1H).

Workup

  1. customthe preparation of I where n=2 and R1=2-furanyl
  2. additionIn a nitrogen-filled glove box
  3. customthe system was flushed 4 times with hydrogen
  4. filtrationAfter 18 h the reaction mixture was filtered through a short pad of silica
  5. customThe solvent was removed at reduced pressure

Sources & evidence

ORD record
ord-51ff4a4e08f34679a06d0158834fba25
Source dataset
uspto-grants-2006_03
Patent number
US07015320B2

Reaction notes

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