1-Bromo-2-methylpropane → tert-butyl N-benzyloxy-N-(2-methylpropyl)carbamate

HRID 976625

Reaction equation

HRID 976625 reaction equation
[H-].[Na+].[CH2:3]([O:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:19](Br)[CH:20]([CH3:22])[CH3:21]>CN(C)C=O>[CH2:3]([O:10][N:11]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 24758Sodium hydrideHCID 736159Tert-butyl N-(benzyloxy)carbamate

Product 1

HCID 19967428tert-butyl N-benzyloxy-N-(2-methylpropyl)carbamateYield 94.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Sodium hydride (0.97 g of 80% in mineral oil, 32 mmol) was added to a solution of tert-butyl N-benzyloxycarbamate (6.53 g, 29 mmol) in N,N-dimethylformamide (45 mL). A gas evolved and the mixture was stirred for 20 minutes. Isobutyl bromide (3.5 mL, 32 mmol) was added and the reaction mixture was heated at 70° C. for 1.5 hr. The reaction was quenched with water (about 50 mL) then extracted twice with diethyl ether. The extracts were combined, washed with water (5 small portions), dried over magnesium sulfate and then concentrated under vacuum to provide 7.63 g of tert-butyl N-benzyloxy-N-(2-methylpropyl)carbamate as a faintly brown oil.

Workup

  1. customThe reaction was quenched with water (about 50 mL)
  2. extractionthen extracted twice with diethyl ether
  3. washwashed with water (5 small portions)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3dd3f6a213ec4bc4b90a3cd5f9f2619b
Source dataset
uspto-grants-1997_03
Patent number
US05612377

Linked notes

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