Diisopropylethylamine → 1-tert-Butyl 4-methyl 4-aminopiperidine-1,4-dicarboxylate

HRID 891012Notes

Reaction equation

HRID 891012 reaction equation
[NH2:1][C:2]1([C:15]([O-:17])=[O:16])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH:18](N(C(C)C)CC)(C)C.C[Si](C=[N+]=[N-])(C)C>C(#N)C.CO>[NH2:1][C:2]1([C:15]([O:17][CH3:18])=[O:16])[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 85702544HCID 85702544, compound

Product 1

HCID 208719401-tert-Butyl 4-methyl 4-aminopiperidine-1,4-dicarboxylateYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

4-Amino-1-tert-butoxycarbonylpiperidine-4-carboxylate (5 g) in acetonitrile (22 ml) and methanol (2 ml) was treated with diisopropylethylamine (3.65 ml) and trimethylsilyldiazomethane (2M in hexane, 13.9 ml). After overnight stirring and evaporation of solvent, the crude product was chromatographed on silica gel (0–50% ethyl acetate/petrol) to give a yellow oil (4 g, 76%).

Workup

  1. customevaporation of solvent
  2. customthe crude product was chromatographed on silica gel (0–50% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-6245b5d095e54e22a47f4b2894917012
Source dataset
uspto-grants-2006_02
Patent number
US07001913B1

Reaction notes

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