Methanol → 3-(Phenylmethyl)-2-piperidinone

HRID 1744399

반응식

HRID 1744399 반응식
[CH:1](=[C:8]1[CH2:13][CH2:12][CH2:11][NH:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>[Ir].ClCCl>[CH2:1]([CH:8]1[CH2:13][CH2:12][CH2:11][NH:10][C:9]1=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 2

HCID 887MethanolHCID 541099263-(Benzylidene)-2-piperidone

생성물 1

HCID 44389953-(Phenylmethyl)-2-piperidinone수율 97.5%

시약·촉매·용매 2

HCID 23924Iridium촉매HCID 6344Dichloromethane용매

실험 절차

This example describes the preparation of I where n=2 and R1=phenyl. In a nitrogen-filled glove box, a Fisher-Porter tube was charged with iridium catalyst prepared as in Example 1 (10 mg, 0.012 mmol) and 3-(benzylidene)-2-piperidone (250 mg, 1.3 mmol). Methanol (3 mL) and dichloromethane (3 mL) were added and the system was flushed 4 times with hydrogen and pressured to 60 psi (0.5 MPa) H2. After 18 h the reaction mixture was filtered through a short pad of silica. The solvent was removed at reduced pressure to afford 3-benzyl-2-piperidone (240 mg, 96%) as a white crystalline solid. Chiral HPLC analysis (Chiralpak AS, 60% heptane, 39.2% isopropanol, 0.4% trifluoroacetic acid, 0.4% n-hexylamine, 40° C.) indicated that conversion was 100% and the enantiomeric excess was 83%. 13C NMR: δ 20.10, 24.33, 36.42, 41.31, 41.74, 125.11, 127.32, 128.21, 138.84, 173.69;

후처리

  1. customthe preparation of I where n=2 and R1=phenyl
  2. additionIn a nitrogen-filled glove box
  3. customthe system was flushed 4 times with hydrogen
  4. filtrationAfter 18 h the reaction mixture was filtered through a short pad of silica
  5. customThe solvent was removed at reduced pressure

출처 및 근거

ORD 기록
ord-ed011945d91c424788ef492129e92999
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07015320B2

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