HCID 59201410, compound → HCID 59201535, compound

HRID 451799Notes

Reaction equation

HRID 451799 reaction equation
[C:1]12([CH2:9][CH:10]([NH:21]C(=O)OCC3C=CC=CC=3)[CH2:11][N:12]([CH3:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2>[OH-].[OH-].[Pd+2].CO>[NH2:21][CH:10]([CH2:9][C:1]12[CH2:2][CH2:3][CH:4]([CH2:5][CH2:6]1)[CH2:7][CH2:8]2)[CH2:11][N:12]([CH3:20])[C:13](=[O:14])[O:15][C:16]([CH3:18])([CH3:19])[CH3:17]

Participants

4

Reactant 1

HCID 59201410HCID 59201410, compound

Product 1

HCID 59201535HCID 59201535, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of benzyl 1-(bicyclo[2.2.2]octan-1-yl)-3-(N-methyl-N-tert-butoxycarbonylamino)propan-2-ylcarbamate (250 mg, 0.58 mmol) and Pd(OH)2 (20%, 60 mg) in 12 Ml of absolute of MeOH was hydrogenated under 20 psi H2 for 2 h. TLC (EtOAc/Petroleum ether=1:2) indicated the completion of reaction. The mixture was then filtered and evaporated to afford tert-butyl 2-amino-3-(bicyclo[2.2.2]octan-1-yl)propyl(methyl)carbamate (150 mg, 87%) as oil, which was used in the next step without further purification.

Workup

  1. customthe completion of reaction
  2. filtrationThe mixture was then filtered
  3. customevaporated

Sources & evidence

ORD record
ord-e430eb9015b9419f8e66e3feacc75b0f
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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