Methanol → HCID 58464056, compound

HRID 1917534Notes

Reaction equation

HRID 1917534 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12](=[O:13])[CH2:11][C:10]([CH3:15])([CH3:14])[C:9]2=[O:16])=[N:6][CH:7]=1.CO.[BH4-].[Na+]>C1COCC1>[OH:16][CH:9]1[N:8]([C:5]2[CH:4]=[CH:3][C:2]([I:1])=[CH:7][N:6]=2)[C:12](=[O:13])[CH2:11][C:10]1([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 57516716HCID 57516716, compound

Product 1

HCID 58464056HCID 58464056, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
2.5 °C

Procedure

(800 mg, 2.42 mmol) 1-(5-Iodopyridin-2-yl)-3,3-dimethylpyrrolidine-2,5-dione (Example 13, step 1) was dissolved in THF (6 ml) and MeOH (2 ml) and the solution was cooled to 0-5° C. NaBH4 (101 mg, 2.67 mmol, 1.1 equiv.) was added at 0-5° C. and the mixture was stirred for 1 hr at 0-5° C. The reaction mixture was extracted with sat. NaHCO3 solution and two times with a small volume of dichloromethane. The crude product was purified by flash chromatography by directly loading the dichloromethane layers onto a amino-silica gel column and eluting with a ethyl acetate/heptane gradient, 0:100 to 100:0. The desired (5-RS)-5-hydroxy-1-(5-iodo-pyridin-2-yl)-4,4-dimethyl-pyrrolidin-2-one (370 mg, 46% yield) was obtained as a white solid, MS: m/e=333.0 (M+H+).

Workup

  1. extractionThe reaction mixture was extracted with sat. NaHCO3 solution and two times with a small volume of dichloromethane
  2. customThe crude product was purified by flash chromatography
  3. washeluting with a ethyl acetate/heptane gradient, 0:100 to 100:0

Sources & evidence

ORD record
ord-7691b92f51704ede96d6df0d74a8fa4e
Source dataset
uspto-grants-2013_12
Patent number
US08618296B2

Reaction notes

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