Ethyl Acetate → tert-butyl [(1S)-2-{[1-(6-hydroxy-1,3-benzoxazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamate

HRID 2368062Notes

Reaction equation

HRID 2368062 reaction equation
[CH3:1][C@H:2]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:3][O:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.C(N(CC)C(C)C)(C)C.Cl[C:29]1[O:30][C:31]2[CH:37]=[C:36]([OH:38])[CH:35]=[CH:34][C:32]=2[N:33]=1.C(OCC)(=O)C>CN(C=O)C>[OH:38][C:36]1[CH:35]=[CH:34][C:32]2[N:33]=[C:29]([N:8]3[CH2:9][CH2:10][CH:5]([O:4][CH2:3][C@@H:2]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH3:1])[CH2:6][CH2:7]3)[O:30][C:31]=2[CH:37]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 234412462-Chloro-1,3-benzoxazol-6-OLHCID 57517479tert-butyl [(1S)-1-methyl-2-(piperidin-4-yloxy)ethyl]carbamate

Product 1

HCID 86658692tert-butyl [(1S)-2-{[1-(6-hydroxy-1,3-benzoxazol-2-yl)piperidin-4-yl]oxy}-1-methylethyl]carbamateYield 95.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl [(1S)-1-methyl-2-(piperidin-4-yloxy)ethyl]carbamate (308 mg) and N,N-diisopropylethylamine (0.311 mL) in DMF (2 mL) was added 2-chloro-1,3-benzoxazol-6-ol (202 mg), and the mixture was stirred at room temperature for 5 hr. Ethyl acetate was added to the reaction mixture, and the mixture was washed with saturated brine and dried over anhydrous sodium sulfate. The extract was applied to silica gel chromatography (NH, ethyl acetate), and concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane/ethyl acetate) to give the title compound (446 mg).

Workup

  1. washthe mixture was washed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-52b817c87b3d4d34b4332b288880853c
Source dataset
uspto-grants-2014_04
Patent number
US08703758B2

Reaction notes

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