cis-4-Hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester → HCID 10103419, compound

HRID 880743Notes

Reaction equation

HRID 880743 reaction equation
[OH:1][C@@H:2]1[CH2:7][CH2:6][N:5](C(OCC2C=CC=CC=2)=O)[C@H:4]([C:18]([O:20][CH3:21])=[O:19])[CH2:3]1>C(O)C.[Pd]>[CH3:21][O:20][C:18]([CH:4]1[CH2:3][CH:2]([OH:1])[CH2:7][CH2:6][NH:5]1)=[O:19]

Participants

4

Reactant 1

HCID 14890235cis-4-Hydroxy-piperidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester

Product 1

HCID 10103419HCID 10103419, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of compound 12 (7 g, 1 eq.) and Pd/C (1.4 g, 20 w %) in dry ethanol (110 mL) was stirred overnight at room temperature under hydrogen. The mixture was filtered, and the filtrate was evaporated to give compound 31 as a yellow oil in quantitative yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.34-1.48 (m, 2H), 1.84 (s, 2H), 1.90-1.96 (m, 1H), 2.27-2.33 (m, 1H), 2.60-2.67 (m, 1H), 3.21 (dt, J=3.86 and 12.79 Hz, 1H), 3.38 (dd, J=3.08 and 10.91 Hz, 1H), 3.70-3.78 (m, 1H), 3.75 (s, 3H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-d7e00760da25416e996b204e522833e4
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

Loading…