(2R,5S)-4-Benzyl-2-methyl-5-(3-oxo-morpholin-4-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester → (2R,5S)-2-Methyl-5-(3-oxo-morpholin-4-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][C:16]2=[O:21])[N:11](CC2C=CC=CC=2)[CH2:10][C@H:9]1[CH3:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][C:16]2=[O:21])[NH:11][CH2:10][C@H:9]1[CH3:29])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Prepared from (2R,5S)-4-benzyl-2-methyl-5-(3-oxo-morpholin-4-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester (1.75 g), acetic acid (8 mL) and Pd/C (1.3 g) using an analogous method to that of Preparation 353. The catalyst was removed by filtration and the solvent was removed in vacuo. The crude material was partitioned between DCM and saturated aqueous NaHCO3. The organic phase was dried over MgSO4 and concentrated in vacuo to give the title compound (870 mg) as a colourless gum. 1H NMR (CDCl3): 4.18 (3H, d), 4.00 (1H, dd), 3.90 (2H, t), 3.70 (1H, d), 3.55-3.37 (2H, m), 3.37-3.16 (3H, m), 3.08 (1H, dd), 2.51 (1H, dd), 2.38-1.78 (1H, m), 1.47 (9H, s), 1.22 (3H, d).
Workup
- customof Preparation 353
- customThe catalyst was removed by filtration
- customthe solvent was removed in vacuo
- customThe crude material was partitioned between DCM and saturated aqueous NaHCO3
- dry with materialThe organic phase was dried over MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-be5362bdd7324771a10401bf8f6a62e9
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018214B2
Reaction notes
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