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Hydrochloric Acid → HCID 11845250, compound

HRID 2216594
Notes
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Reaction equation

HRID 2216594 reaction equation
[Li+].[BH4-].[N+:3]([C:6]1[CH:29]=[CH:28][C:9]([CH2:10][O:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]3[N:20]=[C:21]([C:23](OCC)=[O:24])[CH:22]=[C:16]3[CH2:15]2)=[O:13])=[CH:8][CH:7]=1)([O-:5])=[O:4].Cl.C([O-])([O-])=O.[K+].[K+]>CO.C1COCC1>[N+:3]([C:6]1[CH:29]=[CH:28][C:9]([CH2:10][O:11][C:12]([N:14]2[CH2:19][CH2:18][N:17]3[N:20]=[C:21]([CH2:23][OH:24])[CH:22]=[C:16]3[CH2:15]2)=[O:13])=[CH:8][CH:7]=1)([O-:5])=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 4148881Lithium borohydride2×HCID 11845245HCID 11845245, compound

Product 1

HCID 11845250HCID 11845250, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
2×
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

LiBH4 (640 mg) and MeOH (1.2 mL) was added to the THF (267 mL) solution of 6,7-dihydro-4H-pyrazolo[1,5-a]pyrazine-2,5-dicarboxylic acid 2-ethyl ester 5-(4-nitrobenzyl) ester (10 g) under a nitrogen atmosphere at room temperature and stirred for 3 h at 40° C. Additional LiBH4 (523 mg) and MeOH (1.0 mL) was added to the solution and stirred for 1 h at 40° C. and 1 h at 50° C. The mixture was acidified with 3 mol/L HCl to pH 2 and stirred for 1 h at room temperature, then solid K2CO3 was added to the solution to adjust pH to 8. The insoluble material was filtered off and the filtrate was extracted with AcOEt. The organic layer was dried (K2CO3), and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (CHCl3/MeOH=49/1–19/1) to afford titled compound as pale yellow crystals (8.44 g, 95%).

Workup

  1. stirringstirred for 1 h at 40° C. and 1 h at 50° C
  2. stirringstirred for 1 h at room temperature
  3. filtrationThe insoluble material was filtered off
  4. extractionthe filtrate was extracted with AcOEt
  5. dry with materialThe organic layer was dried (K2CO3)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with silica gel column chromatography (CHCl3/MeOH=49/1–19/1)

Sources & evidence

ORD record
ord-8648e07cd10e45568345bef2d6b2f768
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07112582B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes