Potassium Carbonate → Tert-butyl 4-(((benzyloxy)carbonyl)(ethyl)amino)piperidine-1-carboxylate

HRID 1193413Notes

Reaction equation

HRID 1193413 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9](Cl)=[O:10])=[CH:3][CH:2]=1.C1(C)C=CC=CC=1.[CH2:19]([NH:21][CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1)[CH3:20].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH2:7]([O:8][C:9]([N:21]([CH2:19][CH3:20])[CH:22]1[CH2:23][CH2:24][N:25]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[CH2:26][CH2:27]1)=[O:10])[C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 18374730tert-Butyl 4-(ethylamino)piperidine-1-carboxylateHCID 86663382Cbz-Cl toluene

Product 1

HCID 18677722Tert-butyl 4-(((benzyloxy)carbonyl)(ethyl)amino)piperidine-1-carboxylateYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 50% Cbz-Cl-toluene solution (20.87 ml, 61.40 mmol, 2.0 eq) was added dropwise at 0° C. to a mixture of tert-butyl 4-(ethylamino)piperidine-1-carboxylate (7.0 g, 30.70 mmol, 1.0 eq) and K2CO3 (12.71 g, 92.10 mmol, 3.0 eq) in DCM (100 ml) and the mixture was stirred for 14 hours at RT. The reaction mixture was diluted with DCM (200 ml), washed with water (100 ml) and sat. NaCl solution (100 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 20% ethyl acetate in hexane). Yield: 63% (7.0 g, 19.33 mmol)

Workup

  1. washwashed with water (100 ml) and sat. NaCl solution (100 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by column chromatography (silica gel, 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-941621b5e21f455ab798c88bc2dc1798
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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