Sodium hydride → HCID 86606452, compound

HRID 1811553Notes

Reaction equation

[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([N+]([O-])=O)[CH:5]=[CH:4][N:3]=1.[CH:13]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]1)=[O:18])([CH3:15])[CH3:14].[H-].[Na+]>O1CCOCC1>[CH:13]([O:16][C:17]([N:19]1[CH2:20][CH2:21][CH:22]([O:25][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[C:7]=2[O:8][CH3:9])[CH2:23][CH2:24]1)=[O:18])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-chloro-3-methoxy-4-nitro-pyridine (102.3 mg, 0.543 mmol) and 4-hydroxy-piperidine-1-carboxylic acid isopropyl ester (110 mg, 0.587 mmol) in dioxane (3 mL), sodium hydride (60% dispersion, 32 mg, 0.8 mmol) were added. After stirring at 100° C. for 1 hour, mixture was purified by HPLC to give 4-(2-chloro-3-methoxy-pyridin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester as a white solid (42.0 mg, 24%). 1HNMR (CDCl3, 400 MHz) δ 8.16-8.15 (d, J=5.4 Hz, 1H), 6.92-6.90 (d, J=5.8 Hz), 4.97-4.91 (m, 1H), 4.72-4.68 (m, 1H), 3.91 (s, 3H), 3.75-3.68 (m, 2H), 3.75-3.68 (m, 2H), 3.55 (m, 2H), 2.02-1.85 (m, 4H), 1.27-1.26 (d, J=6.2 Hz, 6H). Exact mass calculated for C15H21ClN2O4 328.12. found 329.2 (MH+).

Workup

custommixture was purified by HPLC

Sources & evidence

ORD record: ord-7497e44f72904e26b16944cdeb29a51c
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362248B2

Reaction notes

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