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

HRID 78506Notes

Reaction equation

HRID 78506 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>C(Cl)Cl>[O:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]1[O:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[S:7][CH:8]=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 87179369Tert-butyl 4-(2-(tetrahydro-2h-pyran-2-yloxy)ethyl)thiazol-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Example 251B (6.3 g, 27.4 mmol) in CH2Cl2 (100 mL) was added commercially available 3,4-dihydro-2H-pyran (Aldrich, 21 g, 250 mmol) and pyridinium-p-toluenesulfonic acid (Aldrich, 3.5 g, 14.0 mmol). The reaction mixture was stirred overnight at room temperature and was diluted with CH2Cl2, washed with water, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography (SiO2, 0-100% ethyl acetate in hexanes) to afford 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 (SiO2, 0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-fb2bee8efa0547ccbd1b656248bb64ac
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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