Methyl iodide → HCID 68469260, compound

HRID 1875360Notes

Reaction equation

HRID 1875360 reaction equation
[OH:1][C@@H:2]1[CH2:8][N:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][C:4]2[S:14][CH:15]=[CH:16][C:3]1=2.[H-].[Na+].[CH3:19]I>C1COCC1>[CH3:19][O:1][C@@H:2]1[CH2:8][N:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][C:4]2[S:14][CH:15]=[CH:16][C:3]1=2

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68469873HCID 68469873, compound

Product 1

HCID 68469260HCID 68469260, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.39 g (14.0 mmol) ethyl (S)-4-hydroxy-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylate in 40 ml THF are mixed batchwise with 0.86 g of 60% NaH mineral oil dispersion while cooling with an ice bath, the mixture is stirred for 15 min and then 1.07 ml methyl iodide are slowly added dropwise. The mixture is stirred for 1 h, poured onto ice water and extracted 3× with ethyl acetate. The combined organic phases are dried with NaSO4 and concentrated.

Workup

  1. temperaturewhile cooling with an ice bath
  2. stirringThe mixture is stirred for 1 h
  3. additionpoured onto ice water
  4. extractionextracted 3× with ethyl acetate
  5. dry with materialThe combined organic phases are dried with NaSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7c5ae49147834b0892b00fa4f8306346
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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