Acetic Acid → 4-(2,2-Dimethoxy-ethylamino)-butyric acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6](=[O:11])[CH2:7][CH2:8][CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:13][O:14][CH:15]([O:18][CH3:19])[CH:16]=O.C(N(CC)CC)C.S([O-])([O-])(=O)=O.[Mg+2].CC(O)=O.C([BH3-])#N.[Na+]>CO>[C:1]([O:5][C:6](=[O:11])[CH2:7][CH2:8][CH2:9][NH:10][CH2:16][CH:15]([O:18][CH3:19])[O:14][CH3:13])([CH3:4])([CH3:2])[CH3:3]Participants
Reactant 7
Product 1
Reagents, catalysts & solvents 1
Procedure
To a cooled solution (0° C.) of 2.94 g (15.00 mmol) of 4-aminobutyric acid ter-butylester; hydrochloride in 75 ml of MeOH were added 2.51 ml (18.00 mmol) of dimethoxyacetaldehyde (45% solution in TBME), 3.86 ml (15.00 mmol) of triethylamine, 16.75 g (135.00 mmol) of magnesium sulfate, 3.43 ml (60.00 mmol) of AcOH and 1.29 g (19.50 mmol) of sodium cyanoborohydride (1.99 g, 31.6 mmol). The reaction was stirred 2 h at RT, another 0.39 ml (1.50 mmol) of dimethoxyacetaldehyde (45% solution in TBME) was added and after 1.5 h, the reaction mixture was partitioned between aqueous saturated NaHCO3 and EtOAc/Et2O (1:1) (3×). The organic phases were washed with aqueous saturated NaHCO3, 10% NaCl and dried over Na2SO4 to yield after evaporation of the solvent 1.87 g (50%) of the titled compound as light yellow oil. MS: 248.18 (MH+).
Workup
- customthe reaction mixture was partitioned between aqueous saturated NaHCO3 and EtOAc/Et2O (1:1) (3×)
- washThe organic phases were washed with aqueous saturated NaHCO3, 10% NaCl
- dry with materialdried over Na2SO4
- customto yield
- customafter evaporation of the solvent 1.87 g (50%) of the titled compound as light yellow oil
Sources & evidence
- ORD record
- ord-e23ce54b219b4916a249ef52a76378f3
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445674B2
Reaction notes
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