Citric Acid → HCID 54473341, compound

HRID 1016420Notes

Reaction equation

HRID 1016420 reaction equation
CC[O:3][C:4]([C:6]1[N:21]=[C:9]2[CH2:10][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:12][CH2:13][N:8]2[N:7]=1)=O.[BH4-].[Li+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:17]([O:16][C:14]([N:11]1[CH2:12][CH2:13][N:8]2[N:7]=[C:6]([CH2:4][OH:3])[N:21]=[C:9]2[CH2:10]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 4148881Lithium borohydrideHCID 58465817HCID 58465817, compound

Product 1

HCID 54473341HCID 54473341, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 5,6-dihydro-8H-[1,2,4]triazolo[1,5-a]pyrazine-2,7-dicarboxylic acid 7-tert-butyl ester 2-ethyl ester (0.90 g, 3.0 mmol), in THF (20 ml) was added lithium borohydride (73 mg, 3.4 mmol), and the resultant mixture was stirred at room temperature overnight. Citric acid solution (10%, 25 ml) was added, then the mixture was washed with dichloromethane (2×50 ml). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with ethyl acetate and then 5% methanol in ethyl acetate, yielding 2-hydroxymethyl-5,6-dihydro-8H-[1,2,4]triazolo[1,5-a]pyrazine-7-carboxylic acid tert-butyl ester as a colourless oil (330 mg). Data for the title compound: 1H NMR (400 MHz, CDCl3) δ 1.50 (9H, s), 2.41 (1H, br s), 3.93 (2H, t, J=5.3 Hz), 4.18 (2H, t, J=5.4 Hz), 4.74 (4H, s); MS (ES+) m/e 255 [MH]+.

Workup

  1. washthe mixture was washed with dichloromethane (2×50 ml)
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel
  5. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-180ad359a08e403fa765b7bc183fa914
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

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