Benzaldehyde → Methyl ((3S,4S)-1-benzyl-4-methylpiperidin-3-yl)carbamate

HRID 7210

반응식

HRID 7210 반응식
[CH3:1][O:2][C:3](=[O:12])[NH:4][C@H:5]1[C@@H:10]([CH3:11])[CH2:9][CH2:8][NH:7][CH2:6]1.[CH:13](=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:12])[NH:4][C@H:5]1[C@@H:10]([CH3:11])[CH2:9][CH2:8][N:7]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6]1

참가 물질

5

반응물 3

HCID 240BenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11557366methyl N-[(3S,4S)-4-methylpiperidin-3-yl]carbamate

생성물 1

HCID 56832346Methyl ((3S,4S)-1-benzyl-4-methylpiperidin-3-yl)carbamate수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
20 °C

실험 절차

The reductive amination of cis-(4-methyl-piperidin-3-yl)-carbamic acid methyl ester was carried out by charging 3.9 grams (1 equiv., 22.6 mmol) to 2.07 ml benzaldehyde (0.9 equiv., 20.4 mmol), 9.6 grams sodium triacetoxyborohydride (2 equivs., 45.3 mmol) and 39 ml methylene chloride (10 volumes). The reaction was stirred at 20° C. and was allowed to exotherm to 30°-35° C. The reaction was complete by GCMS within 30 minutes. The reaction was quenched with 78 ml saturated sodium bicarbonate (20 volumes), extracted into 78 ml methylene chloride (20 volumes) and concentrated to a clear oil. (70% yield). 1H NMR: δ7.2-7.3 (5 H, m, aromatic protons), 5.50-5.48 (1 H, d, J=8.8 Hz), 3.77-3.75 (1 H, d, J=8.0 Hz), 3.63 (3 H, s), 3.45-3.38 (2 H, m), 2.77-2.74 (2 H, d, J=11.2 Hz), 2.14-2.01 (1 H, m), 1.94-1.89 (1 H, m), 1.57-1.55 (1 H, brs), 1.37-1.20 (2 H, m), 0.876 (3 H, d, J=9.2 Hz).

후처리

  1. customto exotherm to 30°-35° C
  2. customThe reaction was quenched with 78 ml saturated sodium bicarbonate (20 volumes)
  3. extractionextracted into 78 ml methylene chloride (20 volumes)
  4. concentrationconcentrated to a clear oil

출처 및 근거

ORD 기록
ord-aa9d08d4a8be45e7b7b7d7d151edf62c
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084277B2

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