1,1'-Thiocarbonyldiimidazole → HCID 89315765, compound

HRID 1497293Notes

Reaction equation

HRID 1497293 reaction equation
[NH2:1][C@H:2]1[C@@H:7]([OH:8])[CH2:6][C@H:5]([CH:9]([F:11])[F:10])[C@@H:4]([OH:12])[C@@H:3]1[OH:13].[C:14](N1C=CN=C1)(N1C=CN=C1)=[S:15]>CN(C=O)C>[F:11][CH:9]([F:10])[C@@H:5]1[C@@H:4]([OH:12])[C@H:3]([OH:13])[C@H:2]2[NH:1][C:14](=[S:15])[O:8][C@H:7]2[CH2:6]1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 117856476HCID 117856476, compound

Product 1

HCID 89315765HCID 89315765, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1R,2R,3S,4S,6S)-3-amino-6-(difluoromethyl)cyclohexane-1,2,4-triol (300 mg, 1.52 mmol) in DMF (3 mL) at room temperature was added thiocarbonyldiimidazole (298 mg, 1.67 mmol). The mixture was stirred at room temperature for 4 h. Solvent was evaporated and the residue was purified by silica gel column chromatography, eluted with 5%-8% MeOH in DCM to give the product (3aR,4R,5R,6S,7aS)-6-(difluoromethyl)-4,5-dihydroxyhexahydrobenzo[d]oxazole-2(3H)-thione (238 mg, 65%) as a white solid. 1H NMR (400 MHz, MeOD) δ 6.20 (t, J=57.4 Hz, 1H), 4.92-4.96 (m, 1H), 3.71 (t, J=7.1 Hz, 1H), 3.26-3.38 (m, 2H), 2.35 (dt, J=15.3 Hz, 3.0 Hz, 1H), 2.03-2.17 (m, 1H), 1.91-1.99 (m, 1H).

Workup

  1. customSolvent was evaporated
  2. customthe residue was purified by silica gel column chromatography
  3. washeluted with 5%-8% MeOH in DCM

Sources & evidence

ORD record
ord-2d3627b1f60640b7aabac86f7f324d16
Source dataset
uspto-grants-2015_12
Patent number
US09199949B2

Reaction notes

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