HCID 49765219、化合物 → tert-Butyl [(3S,5S)-5-methylpiperidin-3-yl]carbamate

HRID 490998ノート

反応式

HRID 490998 の反応式
[C:1]([O:5][C:6](=[O:22])[NH:7][C@H:8]1[CH2:13][C@H:12]([CH3:14])[CH2:11][N:10](CC2C=CC=CC=2)[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([O:5][C:6](=[O:22])[NH:7][C@H:8]1[CH2:13][C@H:12]([CH3:14])[CH2:11][NH:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 1

HCID 49765219HCID 49765219、化合物

生成物 1

HCID 24757764tert-Butyl [(3S,5S)-5-methylpiperidin-3-yl]carbamate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

反応条件

温度
45 °C

実験手順

A 40 L pressure vessel is charged with 0.6 Kg 50% wet, solid palladium on carbon (E101, 10 wt. %) under flow of nitrogen. A solution of 3.2 Kg intermediate (7) in 13.7 Kg of absolute ethanol is then charged to the reactor under nitrogen. The reactor is purged with nitrogen and is then pressurized with hydrogen at 45 psi. The reaction is then heated to 45° C. while maintaining a hydrogen pressure of 45 psi. The reaction is monitored by TLC or LC until complete. The reaction is cooled to ambient temperature, vented, and purged with nitrogen. The reactor contents are filtered through a bed of Celite and the solids are washed with 2.8 Kg of absolute ethanol. The filtrate is concentrated by rotary evaporation under vacuum until a waxy solid is obtained to afford intermediate (8): TLC Rf (Silica F254, 70:30 v/v ethyl acetate-hexanes, KMnO4 stain)=0.12; 1H NMR (300 MHz, CDCl3) δ 5.31 (br s, 1H), 3.80-3.68 (m, 1H), 2.92 (d, J=11.4 Hz, 1H), 2.77 (AB quart, JAB=12.0 Hz, Δv=50.2 Hz, 2H), 2.19 (t, J=10.7 Hz, 1H), 1.82-1.68 (m, 2H), 1.54 (br s, 1H), 1.43 (s, 9H), 1.25-1.15 (m, 1H), 0.83 (d, J=6.6 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 155.3, 78.9, 54.3, 50.8, 45.3, 37.9, 28.4, 27.1, 19.2; MS (ESI+) m/z 215 (M+H), 429 (2M+H).

後処理

  1. additionA 40 L pressure vessel is charged with 0.6 Kg 50% wet
  2. customThe reactor is purged with nitrogen
  3. temperaturewhile maintaining a hydrogen pressure of 45 psi
  4. temperatureThe reaction is cooled to ambient temperature
  5. custompurged with nitrogen
  6. filtrationThe reactor contents are filtered through a bed of Celite
  7. washthe solids are washed with 2.8 Kg of absolute ethanol
  8. concentrationThe filtrate is concentrated by rotary evaporation under vacuum until a waxy solid
  9. customis obtained

出典と根拠

ORDレコード
ord-75c5d98803d740c6a06f83445de6f37e
出典データセット
uspto-grants-2009_05
特許番号
US07528264B2

反応ノート

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