Lithium hydroxide, monohydrate → HCID 86658331, compound

HRID 874920Notes

Reaction equation

HRID 874920 reaction equation
O[Li].[OH2:3].C(OC(=O)[CH2:8][CH:9]1[N:14]2[CH:15]=[C:16]([N+:18]([O-:20])=[O:19])[CH:17]=[C:13]2[C:12](=[O:21])[NH:11][CH2:10]1)C.O1CCCC1.[OH2:28]>>[N+:18]([C:16]1[CH:17]=[C:13]2[C:12](=[O:21])[NH:11][CH2:10][CH:9]([C:8]([OH:28])=[O:3])[N:14]2[CH:15]=1)([O-:20])=[O:19]

Participants

4

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 21881883Oxolane--water (1/1)HCID 131730285HCID 131730285, compound

Product 1

HCID 86658331HCID 86658331, compoundYield 75%

Procedure

LiOH.H2O (27 mg, 1.12 mmol) was added to a solution of ethyl(7-nitro-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl)acetate (V, where R1=OCH2CH3) (0.15 g, 0.56 mmol) in a mixture tetrahydrofuran-water (1:1, 9 mL) and the reaction mixture was stirred at room temperature for 3 h. The organic phase was washed with dichloromethane (2×10 mL). The aqueous phase was acidified with hydrochloric acid (1 M) to reach pH<1 and extracted with EtOAc (3×10 mL). The combined organic layers were dried over Na2SO4 and the solvent was evaporated under vacuum to obtain compound 7-nitro-1-oxo-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazine-4-carboxylic acid (V, where R1=OH) as an off-white solid (101 mg, 75% yield).

Workup

  1. washThe organic phase was washed with dichloromethane (2×10 mL)
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-0282051f876949f5871c5dfe039a146e
Source dataset
uspto-grants-2015_03
Patent number
US08981092B2

Reaction notes

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