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

HRID 252095

반응식

HRID 252095 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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].

후처리

  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

출처 및 근거

ORD 기록
ord-e071172b4f474868a1a3ffe88e94ea76
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868014B2

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