1-Bromo-2-methylpropane → HCID 19753869, compound

HRID 1649907Notes

Reaction equation

HRID 1649907 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][CH2:11][C:12](=[O:20])SC1C=CC=CN=1)[CH3:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:21]([Mg]Br)[CH:22]([CH3:24])[CH3:23].C(Br)C(C)C.[Mg].[Cl-].[NH4+]>O1CCCC1>[C:1]([O:5][C:6]([N:8]([CH2:10][CH2:11][C:12](=[O:20])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH3:9])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 65551-Bromo-2-methylpropaneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 19753844HCID 19753844, compoundHCID 178418816HCID 178418816, compound

Product 1

HCID 19753869HCID 19753869, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of S-2-pyridyl 3-(N-t-butoxycarbonyl-N-methylamino)propanethioate (490 mg) in dry tetrahydrofuran (20 ml) which was cooled to 0° C., was added dropwise a solution of isobutylmagnesium bromide prepared from isobutyl bromide (1.13 g) and magnesium (200 mg) in dry tetrahydrofuran (30 ml), and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was poured into saturated aqueous ammonium chloride (50 ml). The resulting slurry was extracted with diethyl ether (50 ml×2), and the combined extract was dried over magnesium sulfate and concentrated to give 1-(N-t-butoxycarbonyl-N-methylamino)-3-oxo-5-methyl hexane (400 mg) as an oil.

Workup

  1. extractionThe resulting slurry was extracted with diethyl ether (50 ml×2)
  2. extractionthe combined extract
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f4830758659f46ffba82b90ea0da0e11
Source dataset
uspto-grants-1990_05
Patent number
US04921855

Reaction notes

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