Sodium hydride → HCID 67378655, compound

HRID 1182663Notes

Reaction equation

HRID 1182663 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]2[C:5]1=[N:6][C@@H:7]1[CH2:16][CH2:15][CH2:14][C@@H:8]12.C1(C)C=CC(S([CH2:26][N+:27]#[C-:28])(=O)=O)=CC=1>C1COCC1>[CH3:3][N:4]1[C:12](=[O:13])[C:11]2=[CH:26][NH:27][CH:28]=[C:10]2[N:9]2[C@H:8]3[CH2:14][CH2:15][CH2:16][C@H:7]3[N:6]=[C:5]12

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 67379018(3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-one

Product 1

HCID 67378655HCID 67378655, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (95%, 112 mg, 4.44 mmol) is suspended in 3 mL of anhydrous THF, and then a mixture of (3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-one (283 mg, 1.48 mmol) and p-toluenesulfonylmethyl isocyanide (97%, 347 mg, 1.77 mmol) in 5 mL of anhydrous THF is added dropwise. The mixture is stirred at room temperature for an hour, and then quenched with water. The mixture is extracted with CH2Cl2 (5×10 mL). The combined organic phase is washed with brine, and then dried with anhydrous Na2SO4. After filtration, the filtrate is evaporated to dryness under reduced pressure to give crude product (320 mg, yield 94%) as brown solids, which is used for the next reaction without further purification. MS (ESI) m/z 231.1 [M+H]+.

Workup

  1. additionis added dropwise
  2. customquenched with water
  3. extractionThe mixture is extracted with CH2Cl2 (5×10 mL)
  4. washThe combined organic phase is washed with brine
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationAfter filtration
  7. customthe filtrate is evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-8b3379aba6824c2ba9d4af5816ce3efc
Source dataset
uspto-grants-2014_03
Patent number
US08664207B2

Reaction notes

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