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

HRID 7210

反応式

HRID 7210 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
20 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-aa9d08d4a8be45e7b7b7d7d151edf62c
出典データセット
uspto-grants-2006_08
特許番号
US07084277B2

関連ノート

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