Water → N-tert-butoxycarbonyl-N-cyclopropyl-N'-isopropyl-ethane-1,2-diamine

HRID 1970025Notes

Reaction equation

HRID 1970025 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:12][CH:13]=O)[CH:9]([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:15]1([NH2:18])[CH2:17][CH2:16]1.[BH4-].[Na+].O>CO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:1]([O:5][C:6]([N:8]([CH:9]1[CH2:11][CH2:10]1)[CH2:12][CH2:13][NH:18][CH:15]([CH3:17])[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 69828CyclopropylamineHCID 4311764Sodium borohydrideHCID 665248841,1-Dimethylethyl (1-methylethyl)(2-oxoethyl)carbamate

Product 1

HCID 68565196N-tert-butoxycarbonyl-N-cyclopropyl-N'-isopropyl-ethane-1,2-diamineYield 35.2%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent

Procedure

3.9 mL (13 mmol) of titanium isopropoxide and 2 g (10 mmol) of (tert-butoxycarbonyl-isopropyl-amino)-acetaldehyde (prepared according to the method described by Kato, Shiro et al., J. Chem. Soc. Perkin Trans. 1, 1997, 21, 3219-26) are added to a solution of 1.71 g (30 mmol) of cyclopropylamine in 15 mL of anhydrous methanol. The solution is stirred for 5 hours at room temperature then 454 mg (12 mmol) of sodium borohydride is added. Stirring is continued for a further 2 hours then 2 mL of water is added. The reaction mixture is filtered then the solvents are evaporated. The residue is purified by chromatography on silica (eluent dichloromethane/methanol 98/2 then 95/5) to give 852 mg (35%) of N-tert-butoxycarbonyl-N-cyclopropyl-N′-isopropyl-ethane-1,2-diamine in the form of a colourless oil.

Workup

  1. stirringStirring
  2. waitis continued for a further 2 hours
  3. filtrationThe reaction mixture is filtered
  4. customthe solvents are evaporated
  5. customThe residue is purified by chromatography on silica (eluent dichloromethane/methanol 98/2

Sources & evidence

ORD record
ord-a5c72896db1346dd974246a5a2615dbf
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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