Trimethylsilyl iodide → N-[(4aR,7aS)-7a-Phenyl-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide

HRID 338137Notes

Reaction equation

HRID 338137 reaction equation
I[Si](C)(C)C.[C:6]([NH:14][C:15]1[S:16][CH2:17][C@@H:18]2[CH2:23][N:22](C(OCC3C=CC=CC=3)=O)[CH2:21][C@:19]2([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:20]=1)(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(#N)C>[C:34]1([C@:19]23[CH2:21][NH:22][CH2:23][C@H:18]2[CH2:17][S:16][C:15]([NH:14][C:6](=[O:13])[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:20]3)[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86762230benzyl (4aR,7aS)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate

Product 1

HCID 86762229N-[(4aR,7aS)-7a-Phenyl-4a,5,6,7-tetrahydro-4H-pyrrolo[3,4-d][1,3]thiazin-2-yl]benzamideYield 399.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Iodotrimethylsilane (10 mL, 70 mmol) is added to a solution of benzyl (4aR,7aS)-2-benzamido-7a-phenyl-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazine-6-carboxylate (11 g, 23 mmol) in acetonitrile (165 mL), stirred at room temperature for 2 hours and concentrated. The mixture is diluted with water (100 mL) and ethyl acetate (150 mL) and the pH adjusted to 4 with 1 M hydrochloric acid. The aqueous layer is collected. The pH of this aqueous layer is then adjusted to 10 with 2 M sodium hydroxide. The resulting solution is then extracted with ethyl acetate (100 mL), dried over magnesium sulfate and concentrated to give the title compound (31 g, 63%). ES/MS (m/e): 338 (M+H).

Workup

  1. concentrationconcentrated
  2. additionThe mixture is diluted with water (100 mL) and ethyl acetate (150 mL)
  3. customThe aqueous layer is collected
  4. extractionThe resulting solution is then extracted with ethyl acetate (100 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5ff4cb4c010b44619a2bd8a219ddaf33
Source dataset
uspto-grants-2014_11
Patent number
US08889856B2

Reaction notes

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