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Methyl iodide → Tert-butyl 4-(azidomethyl)-4-methoxypiperidine-1-carboxylate

HRID 2407755
Notes
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Reaction equation

HRID 2407755 reaction equation
[N:1]([CH2:4][C:5]1([OH:18])[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1)=[N+:2]=[N-:3].[H-].[Na+].I[CH3:22]>O1CCCC1.O.C(OCC)(=O)C>[N:1]([CH2:4][C:5]1([O:18][CH3:22])[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH2:9][CH2:10]1)=[N+:2]=[N-:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 47002967Tert-butyl 4-(azidomethyl)-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 58504149Tert-butyl 4-(azidomethyl)-4-methoxypiperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 8028
Tetrahydrofuran
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the compound prepared in Example 256 (0.123 g) in tetrahydrofuran (1.5 mL) was added sodium hydride (0.057 g) and iodomethane (0.089 mL) at room temperature. The mixture was stirred at room temperature overnight and then diluted with water and ethyl acetate. The organic layer was dried, evaporated in vacuo and purified by column chromatography on silica gel (5% methanol in dichloromethane) to obtain the title compound (0.071 g) having the following physical data.

Workup

  1. customThe organic layer was dried
  2. customevaporated in vacuo
  3. custompurified by column chromatography on silica gel (5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-dfec709bf44246fba9eb05b7a7b5565b
Source dataset
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08809538B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes