Sodium borohydride → 3-Hydroxy-2,2-dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-propionic acid ethyl ester

HRID 2212561Notes

Reaction equation

HRID 2212561 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6](=[O:31])[C:7]([CH3:30])([CH3:29])[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[C:20]([CH3:28])[CH:19]=2)=[CH:12][CH:11]=1)=[O:9])[CH3:4]>CO>[CH2:3]([O:5][C:6](=[O:31])[C:7]([CH3:30])([CH3:29])[CH:8]([OH:9])[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[C:20]([CH3:28])[CH:19]=2)=[CH:12][CH:11]=1)[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 695965072,2-Dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-3-oxo-propionic acid ethyl ester

Product 1

HCID 695964293-Hydroxy-2,2-dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-propionic acid ethyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.021 g, 0.56 mmol) was added to a solution of 2,2-dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-3-oxo-propionic acid ethyl ester (0.22 g, 0.56 mmol) in methanol (10 mL) under nitrogen at room temperature. The reaction was stirred for 2 h then was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by FCC on silica gel eluting hexane:ethyl acetate (50:50, v:v) to give 3-hydroxy-2,2-dimethyl-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-propionic acid ethyl ester (0.11 g, 50%) as an oil. MS found: (M+H)+=394.

Workup

  1. customthen was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give an oil
  6. customThe product was purified by FCC on silica gel
  7. washeluting hexane:ethyl acetate (50:50, v:v)

Sources & evidence

ORD record
ord-44d9b2ca2abf4fc790c30d7862dcdfc3
Source dataset
uspto-grants-2006_09
Patent number
US07102008B2

Reaction notes

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