(2R,5R)-2-Methoxymethyl-5-methyl-piperazine-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester → tert-butyl (2R,5R)-5-(methoxymethyl)-2-methylpiperazine-1-carboxylate

HRID 1475284Notes

Reaction equation

HRID 1475284 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:13]([CH3:14])[CH2:12][N:11](C(OCC2C=CC=CC=2)=O)[C@@H:10]([CH2:25][O:26][CH3:27])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][C@H:10]([CH2:25][O:26][CH3:27])[NH:11][CH2:12][C@H:13]1[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86723929(2R,5R)-2-Methoxymethyl-5-methyl-piperazine-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester

Product 1

HCID 86723930tert-butyl (2R,5R)-5-(methoxymethyl)-2-methylpiperazine-1-carboxylateYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% Pd/C (5.05 g, 4.76 mmol) and (2R,5R)-2-methoxymethyl-5-methyl-piperazine-1,4-dicarboxylic acid 1-benzyl ester 4-tert-butyl ester (18 g, 48 mmol) were mixed with MeOH (190 mL) at ambient temperature and the mixture was hydrogenated at ambient temperature and 1 bar for 3 h. The mixture was filtered through celite and the filtrate concentrated, to give the title compound (11 g, 99%) as a colourless oil. 1H NMR (Me-d3-OD): 4.16 (1H, dd), 3.80 (1H, d), 3.71-3.47 (1H, m), 3.47-3.40 (1H, m), 3.39 (3H, s), 3.30-3.17 (2H, m), 3.17-3.00 (2H, m), 2.60 (1H, dd), 1.48 (9H, s), 1.25 (3H, d).

Workup

  1. customwas hydrogenated at ambient temperature
  2. filtrationThe mixture was filtered through celite
  3. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-a9f4e912fc8f4b9f9bddca80600cbb10
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

Loading…