Sodium hydride → HCID 86634717, compound

HRID 910913Notes

Reaction equation

[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[H-].[Na+].[Cl:17][C:18]1[CH:23]=[C:22]([N+]([O-])=O)[CH:21]=[CH:20][N:19]=1>>[Cl:17][C:18]1[CH:23]=[C:22]([O:1][CH:2]2[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)[CH:21]=[CH:20][N:19]=1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 5456991-Boc-3-hydroxypiperidine

HCID 7351522-Chloro-4-nitropyridine

Product 1

HCID 86634717HCID 86634717, compoundYield 84.5%

Procedure

Using the method of Example 3, Step A, tert-butyl 3-hydroxypiperidine-1-carboxylate (1.90 g, 9.46 mmol), 60% sodium hydride in mineral oil (378 mg, 9-46 mmol), and 2-chloro-4-nitropyridine (1.50 g, 9.46 mmol) were reacted to provide tert-butyl 3-(2-chloropyridin-4-yloxy)piperidine-1-carboxylate (2.50 g, 84% yield) as an oil. 1H NMR (CDCl3) δ 8.20 (d, 1H), 6.84 (s, 1H), 6.76 (d, 1H), 4.34 (m, 1H), 3.10-4.05 (bm, 4H), 1.50-2.05 (bm; 4H), 1.40 (bs, 9H).

Workup

customwere reacted

Sources & evidence

ORD record: ord-5bd727d5394b440e86abf6f85557a0e5
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022222B2

Reaction notes

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