Benzoyl isothiocyanate → tert-Butyl-1-(benzoylcarbamothioyl)-6a-phenyl-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylate

HRID 338107Notes

Reaction equation

HRID 338107 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([NH:11][O:12][CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22]([N:30]=[C:31]=[S:32])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([N:11]([C:31](=[S:32])[NH:30][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:12][CH2:13]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 86697908tert-Butyl 6a-phenyl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate

Product 1

HCID 86697923tert-Butyl-1-(benzoylcarbamothioyl)-6a-phenyl-3,3a,4,6-tetrahydropyrrolo[3,4-c]isoxazole-5-carboxylateYield 78.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl-6a-phenyl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c]isoxazole-5-carboxylate (1.5 g, 5.2 mmol) in tetrahydrofuran (34 mL) is added benzoyl isothiocyanate (0.84 g, 5.17 mmol). The reaction is stirred for 1 hour at room temperature, concentrated under reduced pressure, and triturated with hexane/ethyl acetate (1:1) to give title compound (1.84 g). The collected solute is purified by silica gel flash chromatography, eluting with hexane/ethyl acetate (1:0) to hexane/ethyl acetate (0:1) to give the title compound, which is combined with the triturated material (2.12 g, 90%). ES/MS (m/e): 454 (M+H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customtriturated with hexane/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-327b64ad94664b398c199ea9a550050d
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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