Methyl iodide → HCID 18187514, compound

HRID 1867369Notes

Reaction equation

HRID 1867369 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].I[CH3:22].OS([O-])(=O)=O.[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([N:14]([C:15]([O:17][CH3:18])=[O:16])[CH3:22])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 23536848HCID 23536848, compound2×

Product 1

HCID 18187514HCID 18187514, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.01 g (3.91 mmol) of 4-methoxycarbonylamino-piperidine-1-carboxylic acid tert-butyl ester (intermediate 38A) in 15 ml of DMF was treated at 0° C. with 0.26 g (5.86 mmol) of NaH (55% in oil) and after 30 min with 1.95 ml (31.28 mmol) of iodomethane. The reaction was stirred for 16 h at RT, neutralized with cold aqueous 10% KHSO4 and extracted with Et2O (3×). The organic phases were washed with aqueous 10% NaCl, dried over Na2SO4 evaporated and purified by flash silica gel column (n-heptane/EtOAc 1:1) to yield 0.99 g (93%) of the title compound as colorless oil. MS: 273.1 (MH+).

Workup

  1. extractionextracted with Et2O (3×)
  2. washThe organic phases were washed with aqueous 10% NaCl
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. custompurified by flash silica gel column (n-heptane/EtOAc 1:1)

Sources & evidence

ORD record
ord-76491b2daa2a429d9574ec3209d34347
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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