Methanol → N-tert-butoxycarbonyl-N-isopropyl-N'-prop-2-ynyl-ethane-1,2-diamine
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].[CH2:15]([NH2:18])[C:16]#[CH:17].CO.[BH4-].[Na+]>O1CCCC1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].O>[C:1]([O:5][C:6]([N:8]([CH:9]([CH3:11])[CH3:10])[CH2:12][CH2:13][NH:18][CH2:15][C:16]#[CH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
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 1.65 g (30 mmol) of propargylamine in 50 mL of anhydrous tetrahydrofuran. The solution is stirred for 5 hours at room temperature then 5 mL of anhydrous methanol and 317 mg (8.4 mmol) of sodium borohydride are 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) to give 1.2 g (50%) of N-tert-butoxycarbonyl-N-isopropyl-N′-prop-2-ynyl-ethane-1,2-diamine in the form of a colourless oil.
Workup
- stirringStirring
- waitis continued for a further 2 hours
- filtrationThe reaction mixture is filtered
- customthe solvents are evaporated
- customThe residue is purified by chromatography on silica (eluent dichloromethane/methanol 98/2)
Sources & evidence
- ORD record
- ord-6b31d377cf104edbac65bbcf77c05d53
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426437B2
Reaction notes
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