HCID 57656859, compound → 1,1-Dimethylethyl (2S)-2-(1-piperazinylmethyl)-4-morpholinecarboxylate

HRID 2371181Notes

Reaction equation

HRID 2371181 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][C@@H:18]2[O:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>[Pd].C(O)C>[N:14]1([CH2:17][C@@H:18]2[O:23][CH2:22][CH2:21][N:20]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19]2)[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1

Participants

4

Reactant 1

HCID 57656859HCID 57656859, compound

Product 1

HCID 576567211,1-Dimethylethyl (2S)-2-(1-piperazinylmethyl)-4-morpholinecarboxylateYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl (2S)-2-({4-[(benzyloxy)carbonyl]piperazin-1-yl}methyl)morpholine-4-carboxylate (11.16 g, 26.6 mmol) was hydrogenated over 10% palladium on carbon (500 mg) in ethanol (100 ml). The catalyst was then filtered off through a pad of celite and filtrate evaporated to dryness to give a dark yellow solid. This was then purified on Isco™ Companion (120 g column: 10% Methanolic ammonia/DCM) to give the product as a pale yellow solid (7.46 g, 26.1 mmol, 98%).

Workup

  1. filtrationThe catalyst was then filtered off through a pad of celite and filtrate
  2. customevaporated to dryness
  3. customto give a dark yellow solid
  4. customThis was then purified on Isco™ Companion (120 g column: 10% Methanolic ammonia/DCM)

Sources & evidence

ORD record
ord-f3758b485017401081f1c2ad5a015527
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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