Piperidine → 4-Amino-4-(1-pyridin-2-yl-cyclopropylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1040550Notes

Reaction equation

HRID 1040550 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([NH:26]C(OCC2C3C=CC=CC=3C3C2=CC=CC=3)=O)([C:14](=[O:25])[NH:15][C:16]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N1CCCCC1>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([NH2:26])([C:14](=[O:25])[NH:15][C:16]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH2:18][CH2:17]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 8082PiperidineHCID 584312364-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(1-pyridin-2-yl-cyclopropylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 584310604-Amino-4-(1-pyridin-2-yl-cyclopropylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of crude 4-(9H-fluoren-9-ylmethoxycarbonylamino)-4-(1-pyridin-2-yl-cyclopropylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester in DMF (0.5 mL) was added piperidine (0.2 mL). The mixture was stirred at room temperature. After 1 h, the solution was diluted with EtOAc (20 mL) and washed with water (4×20 mL). The organic phase was dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting residue was purified via flash chromatography on silica gel (10% MeOH in CH2Cl2 containing 0.1% NH4OH) to afford 74 mg of 4-amino-4-(1-pyridin-2-yl-cyclopropylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester as a white solid.

Workup

  1. washwashed with water (4×20 mL)
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was purified via flash chromatography on silica gel (10% MeOH in CH2Cl2 containing 0.1% NH4OH)

Sources & evidence

ORD record
ord-6df8efb3ce1e4711a35b73c44a60ef67
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

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