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3-Chloro-2-methyl-1-propene → tert-Butyl 4,4-dimethoxy-3-[(2-methyl-2-propen-1-yl)oxy]piperidine-1-carboxylate

HRID 43677
Notes
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Reaction equation

HRID 43677 reaction equation
[OH:1][CH:2]1[C:7]([O:10][CH3:11])([O:8][CH3:9])[CH2:6][CH2:5][N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3]1.[H-].[Na+].Cl[CH2:22][C:23]([CH3:25])=[CH2:24]>CN(C=O)C>[CH3:11][O:10][C:7]1([O:8][CH3:9])[CH2:6][CH2:5][N:4]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:3][CH:2]1[O:1][CH2:24][C:23]([CH3:25])=[CH2:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 112413-Chloro-2-methyl-1-propeneHCID 24758Sodium hydrideHCID 11425480Tert-butyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate

Product 1

HCID 86712356tert-Butyl 4,4-dimethoxy-3-[(2-methyl-2-propen-1-yl)oxy]piperidine-1-carboxylateYield 76.9%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Procedure

The same operation as in Example (90a) was performed using tert-butyl 3-hydroxy-4,4-dimethoxypiperidine-1-carboxylate (5.2 g, 20 mmol), sodium hydride (55% content, 1.31 g, 30 mmol), 3-chloro-2-methyl-1-propene (3.63 g, 40 mmol) and DMF (50 mL). The residue was purified by column chromatography (elution solvent: hexane/ethyl acetate=10/1, 4/1, 2/1) to obtain 4.85 g of the title compound as a colorless oily substance (77%).

Workup

  1. customThe residue was purified by column chromatography (elution solvent: hexane/ethyl acetate=10/1, 4/1, 2/1)

Sources & evidence

ORD record
ord-336b16482f454c9880505ef8c50e2311
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536197B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes