Methyl iodide → HCID 71152272, compound

HRID 1497301Notes

Reaction equation

HRID 1497301 reaction equation
[F:1][C@H:2]1[C@H:7]2[NH:8][C:9](=[S:11])[O:10][C@H:6]2[CH2:5][C@H:4]([CH2:12][OH:13])[C@H:3]1[OH:14].[CH3:15]I.[OH-].[Na+]>CCO>[F:1][C@H:2]1[C@H:7]2[N:8]=[C:9]([S:11][CH3:15])[O:10][C@H:6]2[CH2:5][C@H:4]([CH2:12][OH:13])[C@H:3]1[OH:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 117856679HCID 117856679, compound

Product 1

HCID 71152272HCID 71152272, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3aS,4S,5R,6R,7aS)-4-fluoro-5-hydroxy-6-(hydroxymethyl)hexahydrobenzo[d]oxazole-2(3H)-thione (490 mg, 2.22 mmol) in EtOH (8 mL) was added MeI (630 mg, 4.43 mmol) and 5 N NaOH (0.58 mL, 2.9 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 10%-20% MeOH in DCM to give (3aS,4S,5R,6R,7aS)-4-fluoro-6-(hydroxymethyl)-2-(methylthio)-3a,4,5,6,7,7a-hexahydrobenzo[d]oxazol-5-ol (370 mg, 71%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3) δ 4.78 (ddd, J=52.1 Hz, 3.8 Hz, 1.6 Hz, 1H), 4.64-4.68 (m, 1H), 4.03 (ddd, J=25.8 Hz, 7.6 Hz, 3.9 Hz, 1H), 3.91 (dd, J=10.9 Hz, 3.7 Hz, 1H), 3.61-3.71 (m, 2H), 2.48 (s, 3H), 2.17-2.30 (m, 2H), 1.95-2.02 (m, 1H), 1.65-1.72 (m, 1H).

Workup

  1. customThe solvents were evaporated
  2. customto give the crude product
  3. customThis was purified by SiO2 column
  4. washeluted with 10%-20% MeOH in DCM

Sources & evidence

ORD record
ord-a95010036b96422e9826b0dff03c7ec3
Source dataset
uspto-grants-2015_12
Patent number
US09199949B2

Reaction notes

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