Dimethylformamide → 2-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole

HRID 1020879Notes

Reaction equation

HRID 1020879 reaction equation
[N:1]1[NH:2][CH:3]=[C:4]2[CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][C:5]=12.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].O1[CH2:30][CH2:29]CC1.[CH3:31][S:32](Cl)(=[O:34])=[O:33].CN(C)C=[O:39]>>[C:4]1([S:32]([OH:34])(=[O:39])=[O:33])[CH:5]=[CH:6][CH:30]=[CH:29][CH:8]=1.[CH3:31][S:32]([N:2]1[CH:3]=[C:4]2[CH2:8][NH:7][CH2:6][C:5]2=[N:1]1)(=[O:34])=[O:33]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 31297Methanesulfonyl chlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 178451520HCID 178451520, compound

Product 1

HCID 575185022-(Methylsulfonyl)-2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole

Conditions

Temperature
-30 °C

Procedure

A solution of the product from Step B (100 g, 478 mmol) in anhydrous N,N-dimethylformamide (1.0 L) was cooled to −40° C. and treated with 1 M sodium bis(trimethylsilyl)amide in tetrahydrofuran (502 mL, 502 mmol) slowly over 20 min. The temperature warmed to −30° C. during the addition and the mixture was stirred at this temperature for 1 h. Methanesulfonyl chloride (44.7 mL, 573 mmol) was slowly added via addition funnel and stirred for an additional 1.5 h at −30 to −40° C. The reaction mixture was quenched with ice (3.5 kg), slowly warmed to ambient temperature and stirred for 48 h. The resulting white solid was filtered, washed with water and suction dried to afford the title compound. LC/MS: 288.1 (M+1).

Workup

  1. stirringstirred for an additional 1.5 h at −30 to −40° C
  2. customThe reaction mixture was quenched with ice (3.5 kg)
  3. temperatureslowly warmed to ambient temperature
  4. stirringstirred for 48 h
  5. filtrationThe resulting white solid was filtered
  6. washwashed with water and suction
  7. customdried

Sources & evidence

ORD record
ord-3cfb550558734deca0fcca69a626e7f9
Source dataset
uspto-grants-2014_05
Patent number
US08716482B2

Reaction notes

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