(R)-benzyl 3-((2-hydroxyethyl)(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate → (R)-2-(piperidin-3-yl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethanol

HRID 919573Notes

Reaction equation

HRID 919573 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([C:21]1[C:22]2[CH:29]=[CH:28][N:27]([S:30]([C:33]3[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=3)(=[O:32])=[O:31])[C:23]=2[N:24]=[CH:25][N:26]=1)[C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7](C(OCC2C=CC=CC=2)=O)[CH2:6]1>CCO.[Pd]>[NH:7]1[CH2:8][CH2:9][CH2:10][C@@H:5]([N:4]([C:21]2[C:22]3[CH:29]=[CH:28][N:27]([S:30]([C:33]4[CH:34]=[CH:35][C:36]([CH3:37])=[CH:38][CH:39]=4)(=[O:31])=[O:32])[C:23]=3[N:24]=[CH:25][N:26]=2)[CH2:3][CH2:2][OH:1])[CH2:6]1

Participants

4

Reactant 1

HCID 69676530(R)-benzyl 3-((2-hydroxyethyl)(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Product 1

HCID 69676526(R)-2-(piperidin-3-yl(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)ethanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a stirred solution of (R)-benzyl 3-((2-hydroxyethyl)(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate (1.3 g, 2.4 mmol) in EtOH (10 mL) was added 10% Pd/C (0.8 g) under an atmosphere of N2 and the reaction was placed under an atmosphere of hydrogenated (1 atm.) for 2 h. The mixture was filtered through a celite pad and the filtrate was concentrated in vacuo to afford a residue which was used without further purification (0.9 g, 91%). LCMS [M+1]: 416.

Workup

  1. filtrationThe mixture was filtered through a celite pad
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto afford a residue which
  4. customwas used without further purification (0.9 g, 91%)

Sources & evidence

ORD record
ord-4e040aaf9f7346e8b567dec25cf98d76
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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