Water → HCID 21899503, compound

HRID 1986412Notes

Reaction equation

HRID 1986412 reaction equation
F[B-](F)(F)F.[O:6]=[N+:7]=[O:8].[CH3:9][C:10]([C:19]1[S:20][CH:21]=[C:22]([CH3:24])[CH:23]=1)([CH3:18])[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12].O>C(COC)OC>[CH3:18][C:10]([C:19]1[S:20][C:21]([N+:7]([O-:8])=[O:6])=[C:22]([CH3:24])[CH:23]=1)([CH3:9])[C:11]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12]

Participants

5

Reactant 3

HCID 962WaterHCID 11073463Nitronium tetrafluoroborateHCID 21899441HCID 21899441, compound

Product 1

HCID 21899503HCID 21899503, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Nitronium tetrafluoroborate (0.168 g, 1.26 mmol) was added to a solution of 1-[2-methyl-2-(4-methyl-2-thienyl)propanoyl]pyrrolidine (0.145 g, 0.61 mmol) in dimethoxy ethane (5 ml) cooled to −50 C. The mixture was allowed to warm to −30 C over 1 hour. The mixture was poured into water and extracted with ethyl acetate. The organic layer was separated and washed sequentially with a saturated solution of sodium bicarbonate and then with a saturated brine solution. The ethyl acetate solution was dried over magnesium sulfate and then evaporated to afford 1-[2-methyl-2-(4-methyl-5-nitro-2-thienyl)propanoyl]pyrrolidine as a yellow solid which was used in the next step without purification.

Workup

  1. temperaturecooled to −50 C
  2. temperatureto warm to −30 C over 1 hour
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed sequentially with a saturated solution of sodium bicarbonate
  6. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-0c3f78b57fff437a972daefaeb070b96
Source dataset
uspto-grants-2009_06
Patent number
US07547722B2

Reaction notes

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