HCID 51354609, compound → HCID 25068200, compound

HRID 905949Notes

Reaction equation

HRID 905949 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]>[OH-].[OH-].[Pd+2].CCO>[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 51354609HCID 51354609, compound

Product 1

HCID 25068200HCID 25068200, compoundYield 89.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To ((3R,5R)-1-benzyl-5-methyl-piperidin-3-yl)-carbamic acid tert-butyl ester (prepared as described in WO2004014893) (4.6 g, 15.11 mmol) Pd(OH)2 on carbon (0.46 g) and EtOH (80 mL) were added and the reaction mixture stirred at RT under 1 atm of H2. After 3 hours the palladium was filtered off and the solvent was evaporated. The remaining oil was dried under high vacuum to give 2.9 g of ((3R,5R)-5-methyl-piperidin-3-yl)-carbamic acid tert-butyl ester as an off-white crystalline solid (89% yield).

Workup

  1. filtrationAfter 3 hours the palladium was filtered off
  2. customthe solvent was evaporated
  3. customThe remaining oil was dried under high vacuum

Sources & evidence

ORD record
ord-c5da09e65df7445d980e2f64719e248b
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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