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

HRID 490998노트

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HRID 490998 반응식
[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]

참가 물질

4

반응물 1

HCID 49765219HCID 49765219, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

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온도
45 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-75c5d98803d740c6a06f83445de6f37e
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528264B2

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