Sodium Hydroxide → tert-butyl N-(2-((cyclopropylmethyl)amino)ethyl)carbamate

HRID 349517Notes

Reaction equation

HRID 349517 reaction equation
O=[CH:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].[CH:12]1([CH2:15][NH2:16])[CH2:14][CH2:13]1.[BH4-].[Na+].[OH-].[Na+]>CO>[CH:12]1([CH2:15][NH:16][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 75646CyclopropanemethanamineHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 4311764Sodium borohydride

Product 1

HCID 45092182tert-butyl N-(2-((cyclopropylmethyl)amino)ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl N-(2-oxoethyl)carbamate (1 g) was dissolved in dry methanol (40 ml) and treated with cyclopropane methylamine (0.709 ml) and 4A° molecular sieves (1 g) and the resultant mixture stirred at room temperature for 5 h. Sodium borohydride (0.38 g) was added and the reaction stirred for a further 18 h at room temperature. Sodium hydroxide (2N, 3 ml) was added, the mixture filtered and the filtrate concentrated under reduced pressure. The residue was partitioned between sodium hydroxide solution (2N) and ethyl acetate. The separated organic layer was dried (over magnesium sulphate), filtered and concentrated under reduced pressure to give the title compound (1 g) as a colourless oil

Workup

  1. filtrationthe mixture filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was partitioned between sodium hydroxide solution (2N) and ethyl acetate
  4. dry with materialThe separated organic layer was dried (over magnesium sulphate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dd31f63828ea4f389cd9b73a94c1e6c1
Source dataset
uspto-grants-2007_02
Patent number
US07179835B2

Reaction notes

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