HCID 68954276, compound → Methyl 3-benzyloxy-7-hydroxymethyl-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

HRID 1453844Notes

Reaction equation

HRID 1453844 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:23]([O:25][CH3:26])=[O:24])=[N:11][N:12]2[CH:17]([C:18](O)=[O:19])[CH2:16][N:15]([CH3:21])[C:14](=[O:22])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1>[CH2:1]([O:8][C:9]1[C:10]([C:23]([O:25][CH3:26])=[O:24])=[N:11][N:12]2[CH:17]([CH2:18][OH:19])[CH2:16][N:15]([CH3:21])[C:14](=[O:22])[C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 68954276HCID 68954276, compound

Product 1

HCID 68953014Methyl 3-benzyloxy-7-hydroxymethyl-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-benzyloxy-2-methoxycarbonyl-5-methyl-4-oxo-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine-7-carboxylic acid (183 mg, 0.509 mmol) in anhydrous THF under an atmosphere of nitrogen was added 1M borane-THF complex (6.11 mL, 6.11 mmol). The reaction was stirred at room temperature for 1 hour and quenched with aqueous 6N HCl. The solvent was removed in vacuo, and the resulting residue was purified by reverse phase chromatography on a C-18 column using a gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA). Collection and concentration of the appropriate fractions afforded the alcohol as a sticky, clear oil. 1H NMR (400 MHz, d6-DMSO) δ 7.49-7.47 (m, 2H), 7.39-7.30 (m, 3H), 5.18 (s, 2H), 4.50-4.47 (m, 1H), 4.27 (br s, 1H), 4.07 (dd, J=5.2, 13.6 Hz, 1H), 3.91 (dd, J=5.2, 13.2 Hz, 1H), 3.79 (s, 3H), 3.78-3.71 (m, 2H), 3.03 (s, 3H); ES MS (M+H)=346.

Workup

  1. customquenched with aqueous 6N HCl
  2. customThe solvent was removed in vacuo
  3. customthe resulting residue was purified by reverse phase chromatography on a C-18 column
  4. washa gradient elution of 95-5% H2O (0.1% TFA)/CH3CN (0.1% TFA)
  5. customCollection and concentration of the appropriate fractions

Sources & evidence

ORD record
ord-84dd46d409334319aac0c5aaab0a2497
Source dataset
uspto-grants-2009_01
Patent number
US07476666B2

Reaction notes

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