tert-Butyldimethylsilyl chloride → (1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropylamine
Reaction equation
Cl.[NH2:2][C@@H:3]([C:6]([CH3:9])([OH:8])[CH3:7])[CH2:4][OH:5].[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[NH4+:2].[OH-:5].[Si:10]([O:8][C:6]([CH3:9])([CH3:7])[C@H:3]([NH2:2])[CH2:4][O:5][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]Participants
Reactant 2
Product 2
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
(2R)-2-amino-3-methylbutane-1,3-diol hydrochloride (4.32 g, 27.8 mmol) was dissolved in 10 mL of pyridine and the solution was stirred under N2. tert-Butyldimethylsilyl chloride (16.8 g, 111 mmol) and DMAP (339 mg, 2.8 mmol) were then added and the reaction mixture was heated to 65° C. After 3 days, the reaction was cooled and treated with in 3.5% NaH2PO4 solution. The solution was extracted with 200 mL CH2Cl2 and then with an additional 50 mL of CH2Cl2. The combined organic layers were washed with H2O and brine. The organic layer was then dried over Na2SO4, filtered and concentrate under reduced pressure. Chromatography (SiO2, 3% MeOH/CHCl3 with 0.1% NH4OH) gave (1R)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropylamine (5.85 g) as a light amber oil.
Workup
- temperaturethe reaction was cooled
- extractionThe solution was extracted with 200 mL CH2Cl2
- washThe combined organic layers were washed with H2O and brine
- dry with materialThe organic layer was then dried over Na2SO4
- filtrationfiltered
- concentrationconcentrate under reduced pressure
Sources & evidence
- ORD record
- ord-3b28f641fe3246a693662fa2448238ac
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546383B2
Reaction notes
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