Hydrochloric Acid → methyl 3-(3-(3-(hydroxymethyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate

HRID 1471757Notes

Reaction equation

HRID 1471757 reaction equation
[Si]([O:8][CH2:9][C:10]1[C:11]([C:16]2[CH:20]=[CH:19][N:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[N:17]=2)=[N:12][CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.Cl>CO>[OH:8][CH2:9][C:10]1[C:11]([C:16]2[CH:20]=[CH:19][N:18]([CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[N:17]=2)=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86690794methyl 3-(3-(3-((tert-butyldimethylsilyloxy)methyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate

Product 1

HCID 86690795methyl 3-(3-(3-(hydroxymethyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoateYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl 3-(3-(3-((tert-butyldimethylsilyloxy)methyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate in MeOH (10 mL) was added HCl (2 N, 1.2 mL, 10 eq.). The mixture was stirred at rt for 4 h, concentrated, neutralized to pH 7-8 with NaHCO3(sat) solution, and extracted with EtOAc three times. The combined organic layers were washed with brine, dried over Na2SO4, concentrated, and purified on silica gel using EtOAc as eluent to give methyl 3-(3-(3-(hydroxymethyl)pyridin-2-yl)-1H-pyrazol-1-yl)propanoate (51 mg, 67%) as an oil. LRMS (M+H+) m/z 262.1.

Workup

  1. concentrationconcentrated
  2. extractionextracted with EtOAc three times
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified on silica gel

Sources & evidence

ORD record
ord-46eaac205c0648c0bff04310210b8d8d
Source dataset
uspto-grants-2015_04
Patent number
US09012450B2

Reaction notes

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