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

HRID 273271Notes

Reaction equation

HRID 273271 reaction equation
[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]

Participants

4

Reactant 1

HCID 49765219HCID 49765219, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

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) δ5.31 (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).

Workup

  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

Sources & evidence

ORD record
ord-19e45ebbb7284043a55cdb89031b0e64
Source dataset
uspto-grants-2008_11
Patent number
US07456279B2

Reaction notes

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