HCID 66999754, compound → HCID 66999588, compound

HRID 559352Notes

Reaction equation

HRID 559352 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:10](=[O:23])[C@H:9]1[CH2:24][O:25]CC1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:10](=[O:23])[C@H:9]1[CH2:24][OH:25])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 66999754HCID 66999754, compound

Product 1

HCID 66999588HCID 66999588, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of (R)-2-benzyloxymethyl-3-oxo-4-(3-piperidin-1-yl-propyl)-piperazine-1-carboxylic acid tert-butyl ester (321 mg, 0.72 mmol) in acetic acid (9 ml) was stirred for 18 h at room temperature under a hydrogen atmosphere (3 bar) in the presence of palladium (10% on activated charcoal, 161 mg), then insoluble material was removed by filtration and the filtrate evaporated. The residue was partitioned between ethyl acetate and 2 M aq. sodium carbonate solution. The organic layer was dried (MgSO4), filtered, and evaporated to afford the title compound (200 mg, 78%). Light brown oil, MS (ISP)=356.4 (M+H)+.

Workup

  1. custominsoluble material was removed by filtration
  2. customthe filtrate evaporated
  3. customThe residue was partitioned between ethyl acetate and 2 M aq. sodium carbonate solution
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-7139270a0dab4e5ca748332abdde5330
Source dataset
uspto-grants-2011_11
Patent number
US08063042B2

Reaction notes

Loading…