Water → N-Boc-1-methoxy-2-methyl-2-propanamine

HRID 636732Notes

Reaction equation

HRID 636732 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]([CH3:15])([CH3:14])[CH2:12][OH:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:16]I.O>C1COCC1>[C:3]([O:7][C:8]([NH:10][C:11]([CH3:15])([CH3:14])[CH2:12][O:13][CH3:16])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 14578673tert-butyl N-(1-hydroxy-2-methylpropan-2-yl)carbamate

Product 1

HCID 21255687N-Boc-1-methoxy-2-methyl-2-propanamineYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

A suspension of 60% NaH (635.7 mg, 15.89 mmol) in THF (10 ml) was cooled to 0° C. To the mixture was added a solution of 2-t-butoxycarbonylamino-2-methyl-1-propanol (1.5398 g, 8.14 mmol) in THF (5 ml) dropwise, and stirred for 1.5 hours. To the mixture was added a solution of methyl iodide (0.50 ml, 8.03 mmol) in THF (5 ml) dropwise at 0° C., and stirred for 2.5 hours. The reaction mixture was added to water and extracted three times with ethyl acetate. The extract was dried over MgSO4, concentrated and purified by silica gel chromatography (hexane/ethyl acetate=5/1-0/1) to give the title compound (422 mg; 26%).

Workup

  1. stirringstirred for 2.5 hours
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe extract was dried over MgSO4
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (hexane/ethyl acetate=5/1-0/1)

Sources & evidence

ORD record
ord-d9c15020481e49948b0feb5d3c57b6e1
Source dataset
uspto-grants-2001_02
Patent number
US06194461B1

Reaction notes

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