Tetrahydrofuran → HCID 85821897, compound

HRID 891567Notes

Reaction equation

HRID 891567 reaction equation
O[CH:2]1[CH2:7][CH2:6][CH2:5][NH:4][CH2:3]1.[CH2:8]([O:10][C:11]([N:13]=[C:14]=[S:15])=[O:12])[CH3:9].[O:16]1CCCC1>>[CH2:8]([O:10][C:11](=[O:12])[NH:13][C:14]([N:4]1[CH2:5][CH2:6][CH:7]([OH:16])[CH2:2][CH2:3]1)=[S:15])[CH3:9]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 232933-HydroxypiperidineHCID 85320Ethyl isothiocyanatoformate

Product 1

HCID 85821897HCID 85821897, compoundYield 100%

Procedure

To a solution of 3-hydroxypiperidine (1.0 g, 9.89 mmol) in tetrahydrofuran (50 ml) was added ethoxycarbonyl isothiocyanate (1.4 ml, 11.9 mmol) in an ice bath. The reaction mixture was brought to room temperature in 10 minutes and then stirred overnight. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column using toluene:ethyl acetate (1:2) as the eluant to afford (4-hydroxypiperidine-1-carbothioyl)carbamic acid ethyl ester (2.3 g, yield 100%) as a yellow oil.

Workup

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-65f573d6cf24409cab0679d2e43d4e63
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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