3,4-dihydro-2H-pyran → Tert-butyl 4-[2-(tetrahydro-2h-pyran-4-yloxy)ethyl]-1,3-thiazol-2-ylcarbamate

HRID 1028167Notes

Reaction equation

HRID 1028167 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[S:7][CH:8]=1.[O:17]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18]1.[NH+]1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[O:17]1[CH2:22][CH2:21][CH:20]([O:1][CH2:2][CH2:3][C:4]2[N:5]=[C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[S:7][CH:8]=2)[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 22033616Pyridinium.p-toluenesulfonateHCID 22405510tert-Butyl (4-(2-hydroxyethyl)thiazol-2-yl)carbamate

Product 1

HCID 87745583Tert-butyl 4-[2-(tetrahydro-2h-pyran-4-yloxy)ethyl]-1,3-thiazol-2-ylcarbamateYield 82.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 3B (6.3 g, 27.4 mmol) in dichloromethane (100 mL) were added commercially available 3,4-dihydro-2H-pyran (purchased from Aldrich) (21 g, 250 mmol) and pyridinium-p-toluenesulfonic acid (purchased from Aldrich) (3.5 g, 14.0 mmol). The reaction mixture was stirred overnight at room temperature and then diluted with dichloromethane, washed with water, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using an Analogix® IT280™ (SiO2, 0-100% ethyl acetate in hexanes) to afford 7.4 g (82%) of the title compound. MS (ESI+) m/z 329 (M+H)+

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e186c89aca8e4009b76a7dad869987e9
Source dataset
uspto-grants-2014_05
Patent number
US08735434B2

Reaction notes

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