1,1'-Thiocarbonyldiimidazole → HCID 117856679, compound

HRID 1497300Notes

Reaction equation

HRID 1497300 reaction equation
[NH2:1][C@@H:2]1[C@H:7]([F:8])[C@H:6]([OH:9])[C@@H:5]([CH2:10][OH:11])[CH2:4][C@@H:3]1[OH:12].[C:13](N1C=CN=C1)(N1C=CN=C1)=[S:14]>CN(C=O)C>[F:8][C@H:7]1[C@H:2]2[NH:1][C:13](=[S:14])[O:12][C@H:3]2[CH2:4][C@H:5]([CH2:10][OH:11])[C@H:6]1[OH:9]

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 89315948HCID 89315948, compound

Product 1

HCID 117856679HCID 117856679, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (1S,2S,3S,4R,5R)-2-amino-3-fluoro-5-(hydroxymethyl)cyclohexane-1,4-diol (480 mg, 2.68 mmol) in DMF (5 mL) at room temperature was added thiocarbonyldiimidazole (549 mg, 3.08 mmol). The mixture was stirred at room temperature for 1.5 h. Solvent was evaporated and the residue was purified by silica gel column chromatography, eluted with 10%-35 MeOH in DCM to give the product (3aS,4S,5R,6R,7aS)-4-fluoro-5-hydroxy-6-(hydroxymethyl)hexahydrobenzo[d]oxazole-2(3H)-thione (494 mg, 83%) as a pale yellow solid. 1H NMR (500 MHz, MeOD) δ 4.74-4.77 (m, 1H), 4.56 (ddd, J=52.8 Hz, 3.8 Hz, 1.7 Hz, 1H), 3.98 (ddd, J=23.3 Hz, 7.0 Hz, 3.9 Hz, 1H), 3.59-3.64 (m, 2H), 3.45 (ddd, J=29.6 Hz, 10.6 Hz, 1.5 Hz, 1H), 2.22-2.27 (m, 1H), 1.95-2.02 (m, 1H), 1.69-1.75 (m, 1H).

Workup

  1. customSolvent was evaporated
  2. customthe residue was purified by silica gel column chromatography
  3. washeluted with 10%-35 MeOH in DCM

Sources & evidence

ORD record
ord-e24b090254544151b1ca404089f2e065
Source dataset
uspto-grants-2015_12
Patent number
US09199949B2

Reaction notes

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