1-Bromo-3-methylbutane → N-t-butoxycarbonyl-N-methylamino-2-hydroxy-5-methylhexane
Reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][CH:11]=[O:12])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:13]([Mg]Br)[CH2:14][CH:15]([CH3:17])[CH3:16].C(Br)CC(C)C.[Mg].[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]([CH2:10][CH:11]([OH:12])[CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-t-butoxycarbonylsarcosinal (3.46 g) in dry tetrahydrofuran (100 ml) which was cooled to -78° C., was added dropwise a solution of isopentylmagnesium bromide prepared from isopentyl bromide (30.8 g) and magnesium (4.86 g) in dry tetrahydrofuran (200 ml). After the addition was complete, the reaction mixture was allowed to warm to ambient temperature and stirred at the same temperature for 4 hours. After saturated aqueous ammonium chloride (200 ml) was added thereto, the resulting mixture was extracted with diethyl ether (300 ml×2). The combined extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified with silicagel column chromatography (20% ethylacetate in n-hexane as eluent) to give 1-(N-t-butoxycarbonyl-N-methylamino)-2-hydroxy5-methylhexane (3.96 g).
Workup
- additionAfter the addition
- extractionthe resulting mixture was extracted with diethyl ether (300 ml×2)
- extractionThe combined extract
- dry with materialwas dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified with silicagel column chromatography (20% ethylacetate in n-hexane as eluent)
Sources & evidence
- ORD record
- ord-0cacf66ee7654e96a76e1bf72f2faf89
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04921855
Reaction notes
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