Isobutyl iodide → tert-butyl [(1S)-1-methyl-2-({1-[6-(2-methylpropoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)ethyl]carbamate

HRID 2368115Notes

Reaction equation

HRID 2368115 reaction equation
[OH:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([N:9]3[CH2:14][CH2:13][CH:12]([O:15][CH2:16][C@@H:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:18])[CH2:11][CH2:10]3)[O:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:36][CH:37]([CH3:39])[CH3:38]>CN(C=O)C.C(OCC)(=O)C>[CH3:18][C@H:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:16][O:15][CH:12]1[CH2:11][CH2:10][N:9]([C:7]2[O:8][C:4]3[CH:3]=[C:2]([O:1][CH2:36][CH:37]([CH3:39])[CH3:38])[CH:28]=[CH:27][C:5]=3[N:6]=2)[CH2:14][CH2:13]1

Participants

6

Reactant 3

HCID 10556Isobutyl iodideHCID 11430Potassium CarbonateHCID 86658692tert-butyl [(1S)-2-{[1-(6-hydroxy-1,3-benzoxazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate

Product 1

HCID 86658705tert-butyl [(1S)-1-methyl-2-({1-[6-(2-methylpropoxy)-1,3-benzoxazol-2-yl]piperidin-4-yl}oxy)ethyl]carbamateYield 56.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl [(1S)-2-{[1-(6-hydroxy-1,3-benzoxazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate (150 mg) in DMF (5 mL) were added potassium carbonate (210 mg) and 1-iodo-2-methylpropane (190 mg), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (97 mg).

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c1854de004b54e65a523d53dc7a4a998
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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