1-Bromo-2-methylpropane → HCID 86690656, compound

HRID 1505625Notes

Reaction equation

HRID 1505625 reaction equation
Br[CH2:2][CH:3]([CH3:5])[CH3:4].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]([NH:15][S:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:18])=[O:17])[CH3:14])=[CH:9][CH:8]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([C@H:13]([N:15]([CH2:2][CH:3]([CH3:5])[CH3:4])[S:16]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)(=[O:18])=[O:17])[CH3:14])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 65551-Bromo-2-methylpropaneHCID 10796Cesium carbonateHCID 33037884HCID 33037884, compound

Product 1

HCID 86690656HCID 86690656, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

1-Bromo-2-methylpropane (10.1 g, 73 mmol) was added into a solution of (R)—N-(1-(4-bromophenyl)ethyl)(phenyl)methanesulfonamide (13 g, 36.7 mmol) and Cs2CO3 (23.8 g, 73 mmol) in DMF (150 mL) dropwise at 0° C. The mixture was then stirred at 80° C. for 20 h before it was cooled to ambient temperature. The mixture was filtered and the filtrate was concentrated in vacuo to remove the solvent. The residue was dissolved with DCM (100 mL) and washed with water (100 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give a residue which was purified on silica gel chromatography (petroleum ether: ethyl acetate=10:1) to provide (R)—N-(1-(4-bromophenyl)ethyl)-N-isobutyl(phenyl)methanesulfonamide (10.8 g, 72% yield) as colorless oil. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.71 (d, 3H), 0.77 (d, 3H), 1.48 (d, 3H), 1.60-1.66 (m, 1H), 2.77-2.83 (m, 2H), 4.11-4.22 (m, 2H), 4.94-4.96 (m, 2H), 7.24-7.48 (m, 9H); >99% ee value (Chiral-HPLC, 214 nm).

Workup

  1. temperaturewas cooled to ambient temperature
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto remove the solvent
  5. dissolutionThe residue was dissolved with DCM (100 mL)
  6. washwashed with water (100 mL)
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a residue which
  11. customwas purified on silica gel chromatography (petroleum ether: ethyl acetate=10:1)

Sources & evidence

ORD record
ord-05689198f168450ea4ee5db852a0dd0b
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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