(S)-1-Methyl-5-((pyridin-3-yloxy)methyl)pyrrolidin-2-one → HCID 54567930, compound

HRID 1416646Notes

Reaction equation

[CH3:1][N:2]1[C@H:6]([CH2:7][O:8][C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:5][CH2:4][C:3]1=O.[CH3:16][Li]>CCOCC>[CH3:1][N:2]1[CH:3]([CH3:16])[CH2:4][CH2:5][C@H:6]1[CH2:7][O:8][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A 1.24 g (6.0 mmol) sample of 3-(1-methyl-2-oxo-5-(S)-pyrrolidinylmethoxy)-pyridine, prepared as in Example 22b above, was dissolved in 50 mL of ether and cooled to -78° C. To this solution was added 4.71 mL (6.6 mmol) of methyl lithium, and the solution was warmed to room temperature and stirred for 2 hours. The solution was cooled to 0° C., 66 mL of a 1M solution of LAlH4 was added, and the reaction mixture was stirred for 2 hours at room temperature. The reaction was quenched by addition of 1 mL of methanol, the solvents removed, and the residue purified by chromatography on silica gel, eluting with 200:1 to 100:1 chloroform:methanol. MS (DCI/NH3) m/e: 207 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ: 83.4-8.30 (m, 1H), 8.24-8.17 (m, 1H), 7.25-7.27 (m, 2H), 4.08-4.03 (m, 1H), 3.93-3.87 (m, 1H), 2.83-2.73 (m, 1H), 2.43 (s, 3H), 2.43-2.35 (m, 1H), 2.03-1.82 (m, 2H), 1.70-1.40 (m, 2H), 1.13 (d, J=6.7 Hz, 3H).

Workup

temperaturethe solution was warmed to room temperature
temperatureThe solution was cooled to 0° C.
stirringthe reaction mixture was stirred for 2 hours at room temperature
customThe reaction was quenched by addition of 1 mL of methanol
customthe solvents removed
customthe residue purified by chromatography on silica gel
washeluting with 200:1 to 100:1 chloroform

Sources & evidence

ORD record: ord-9a5c85732b1d4efd89708a547c5f0518
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05914328

Reaction notes

Loading…