Tetrahydrofuran → HCID 18621466, compound

HRID 1861780Notes

Reaction equation

HRID 1861780 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14](OC)=[O:15])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[BH4-].[Na+].[Li+].[Cl-]>CCO>[CH2:1]([C:8]1[CH:13]=[CH:12][N:11]=[C:10]([CH2:14][OH:15])[CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 111177772-Pyridinecarboxylic acid, 4-(phenylmethyl)-, methyl ester

Product 1

HCID 18621466HCID 18621466, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl 4-benzyl-picolinate (5.80 g, 26.0 mmol) in EtOH (100 mL)/THF (66 mL) was added a mixture of NaBH4 (1.90 g, 51.0 mmol) and LiCl (2.16 g, 51.0 mmol). The resulting mixture was stirred at 25° C. for 4 h then concentrated under reduced pressure, diluted with brine (200 mL) and extracted with EtOAc (2×200 mL). The collected organic phase was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The crude compound was purified by flash chromatography on silica gel using EtOAc/n-hexane as eluant to afford the title compound as a pale yellow oil (4.4 g, 80%). 1H NMR (CDCl3) δ3.8 (bs, 1H), 3.97 (s, 2H), 4.70 (s, 2H), 7.03 (d, J=4.5 Hz, 1H), 7.06 (s, 1H), 7.17 (d, J=6.9 Hz, 2H), 7.20-7.40 (m, 3H), 8.43 (d, J=4.8 Hz, 1H).

Workup

  1. concentrationthen concentrated under reduced pressure
  2. additiondiluted with brine (200 mL)
  3. extractionextracted with EtOAc (2×200 mL)
  4. washThe collected organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude compound was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-095e16a7e4c6416580308402f6b9666c
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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