Methyl iodide → HCID 71152509, compound

HRID 1497294Notes

Reaction equation

HRID 1497294 reaction equation
[F:1][CH:2]([F:15])[C@@H:3]1[C@@H:12]([OH:13])[C@H:11]([OH:14])[C@H:6]2[NH:7][C:8](=[S:10])[O:9][C@H:5]2[CH2:4]1.[CH3:16]I.[OH-].[Na+]>CCO>[F:15][CH:2]([F:1])[C@@H:3]1[C@@H:12]([OH:13])[C@H:11]([OH:14])[C@H:6]2[N:7]=[C:8]([S:10][CH3:16])[O:9][C@H:5]2[CH2:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 89315765HCID 89315765, compound

Product 1

HCID 71152509HCID 71152509, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3aR,4R,5R,6S,7aS)-6-(difluoromethyl)-4,5-dihydroxyhexahydrobenzo[d]oxazole-2(3H)-thione (233 mg, 0.97 mmol) in EtOH (5 mL) was added MeI (277 mg, 1.95 mmol) and 5 N NaOH (0.21 mL, 1.1 mmol). The mixture was stirred at room temperature for 2 h. The solvents were evaporated to give the crude product. This was purified by SiO2 column, eluted with 3%-5% MeOH in DCM to give (3aR,4R,5R,6S,7aS)-6-(difluoromethyl)-2-(methylthio)-3a,4,5,6,7,7a-hexahydrobenzo[d]oxazole-4,5-diol (218 mg, 88%) as a pale yellow solid. MS m/z 254.1 (M+1, 100%); 1H NMR (400 MHz, MeOD) δ 6.16 (td, J=56.8 Hz, 1.8 Hz, 1H), 4.79-4.83 (m, 1H), 3.85 (t, J=7.6 Hz, 1H), 3.39 (t, J=9.0 Hz, 1H), 3.28 (t, J=7.9 Hz, 1H), 2.48 (s, 3H), 2.27 (dt, J=14.7 Hz, 3.6 Hz, 1H), 1.91-2.10 (m, 2H).

Workup

  1. customThe solvents were evaporated
  2. customto give the crude product
  3. customThis was purified by SiO2 column
  4. washeluted with 3%-5% MeOH in DCM

Sources & evidence

ORD record
ord-5a214e31e8a649d2a60ef30527b2c84c
Source dataset
uspto-grants-2015_12
Patent number
US09199949B2

Reaction notes

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