1-Benzyl-3-pyrrolidinone → 1-Benzyl-3-methylpyrrolidin-3-OL

HRID 252095

Reaction equation

HRID 252095 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:14][Mg]Br>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([CH3:14])([OH:13])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 698901-Benzyl-3-pyrrolidinoneHCID 178418573HCID 178418573, compound

Product 1

HCID 186296481-Benzyl-3-methylpyrrolidin-3-OL

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Add 1-benzyl-3-pyrrolidinone (10 g, 61.7 mmol) in dry THF (40 mL) to methyl magnesium bromide (3 M in diethyl ether, 44 mL, 132 mmol) at −20° C. Stir for 3 h and allow the reaction to warm up to 0° C. Pour onto crushed ice and extract with diethyl ether. Combine the organic layers and wash with saturated aqueous sodium chloride, dry (magnesium sulfate) and concentrate to give 1-benzyl-3-methylpyrrolidin-3-ol which may be used directly in the next step without further purification (8.6 g, 73%). 1H NMR (400 MHz, CDCl3) δ 7.22-7.33 (5H, m), 3.63 (2H, s), 2.92-2.99 (1H, m), 2.71 (1H, d, J=9.29 Hz), 2.28-2.36 (1H, m), 2.22 (1H, d, J=9.78 Hz), 1.84-1.91 (2H, m), 1.33 (3H, s), MS (ES): m/z=192 [M+H].

Workup

  1. customthe reaction
  2. additionPour
  3. customonto crushed ice
  4. extractionextract with diethyl ether
  5. washwash with saturated aqueous sodium chloride
  6. dry with materialdry (magnesium sulfate)
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-e071172b4f474868a1a3ffe88e94ea76
Source dataset
uspto-grants-2011_01
Patent number
US07868014B2

Linked notes

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