Reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[CH:11]1([O:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[NH2:19])[CH2:15][CH2:14][CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OCC)(=O)C>ClC(Cl)C>[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH:19][C:18]([CH3:21])([C:17]([O:16][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:22])[CH3:20]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-(bromomethyl)-benzaldehyde (0.503 g, 2.52 mmol) in dichloroethane (20 mL) was added α,α-dimethylglycine cyclopentyl ester (0.893 g, 5.2 mmol) and sodium triacetoxyborohydride (1.47 g, 6.9 mmol). The mixture was stirred at room temperature for 3 hours, then poured into ethyl acetate (200 mL) and washed with saturated ammonium chloride solution (3 times 50 mL). The organic fraction was dried (MgSO4), concentrated and purified by flash column chromatography (SiO2, 7:3 heptane:ethyl acetate) to yield the desired product (0.350 g, 39% yield). LC/MS: m/z 354/356 [M+H]+
Workup
- washwashed with saturated ammonium chloride solution (3 times 50 mL)
- dry with materialThe organic fraction was dried (MgSO4)
- concentrationconcentrated
- custompurified by flash column chromatography (SiO2, 7:3 heptane:ethyl acetate)
Sources & evidence
- ORD record
- ord-12968c7296d848ee993da33f3dbf7c2e
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09321718B2
Linked notes
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