Methyl iodide → 2-(Isobutoxycarbonyl-methyl-amino)-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid tert-butyl ester

HRID 1243146Notes

Reaction equation

HRID 1243146 reaction equation
[C:1]([O:5][C:6]([C:8]1([NH:18][C:19]([O:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[O:20])[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26]I.[H-].[Na+]>CN(C=O)C.[NH4+].[Cl-]>[C:1]([O:5][C:6]([C:8]1([N:18]([C:19]([O:21][CH2:22][CH:23]([CH3:25])[CH3:24])=[O:20])[CH3:26])[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 695850442-Isobutoxycarbonylamino-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid tert-butyl ester

Product 1

HCID 695851042-(Isobutoxycarbonyl-methyl-amino)-1,2,3,4-tetrahydro-naphthalene-2-carboxylic acid tert-butyl esterYield 83.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

The carbamate from Example 33D (1.5 g, 4.3 mmol) was dissolved in DMF (4.0 mL) followed by addition of MeI (1.1 g, 8.0 mmol) and NaH (50%, 384 mg, 8.0 mmol) at 0° C. The mixture was stirred for 6 hours, diluted with aqueous NH4Cl and extracted with ethyl acetate(3×75 mL). The combined organic layers were dried with MgSO4, filtered, concentrated under reduced pressure to provide the titled compound (1.3 g, 83%).

Workup

  1. extractionextracted with ethyl acetate(3×75 mL)
  2. dry with materialThe combined organic layers were dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d2c0df5dc6fb4bf0abeb646cecb2e90f
Source dataset
uspto-grants-2006_10
Patent number
US07115767B2

Reaction notes

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