Tetrahydrofuran → 1-Benzyl-3-methylpyrrolidin-3-OL

HRID 1496684Notes

Reaction equation

HRID 1496684 reaction equation
[CH2:1]([N:8]1CCC[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][Mg]Br.[CH2:17]1C[O:20][CH2:19][CH2:18]1>>[CH2:1]([N:8]1[CH2:17][CH2:18][C:19]([CH3:14])([OH:20])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 791761-Benzyl-3-pyrrolidoneHCID 178418573HCID 178418573, compound

Product 1

HCID 186296481-Benzyl-3-methylpyrrolidin-3-OLYield 58.1%

Conditions

Temperature
-20 °C

Procedure

1-benzylpyrrolidone (1.1 g, 6.3 mmol) was dissolved in 4 mL THF under stirring at −20° C. The resulting solution was dropwisely added to a solution of methyl magnesium bromide (13.2 mL, 12.2 mmol) in THF. The stirring was continued for 3 hours. After the completion of reaction, the reaction solution was dropwisely added to an ice water. The resulting mixture was washed with a saturated aqueous NaCl solution, dried over Na2SO4, and purified by column chromatography (silica gel column, eluted with petroleum ether: ethyl acetate=20:1 (volumetric ratio)) to produce the product of 1-benzyl-3-methylpyrrolidinyl-3-ol (0.7 g) in a yield of 58.1%.

Workup

  1. customAfter the completion of reaction
  2. washThe resulting mixture was washed with a saturated aqueous NaCl solution
  3. dry with materialdried over Na2SO4
  4. custompurified by column chromatography (silica gel column, eluted with petroleum ether: ethyl acetate=20:1 (volumetric ratio))
  5. customto produce the product of 1-benzyl-3-methylpyrrolidinyl-3-ol (0.7 g) in a yield of 58.1%

Sources & evidence

ORD record
ord-10ce34f5a57644c6bb2be09881066810
Source dataset
uspto-grants-2015_12
Patent number
US09198902B2

Reaction notes

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