1-Carbobenzoxy-4-piperidinecarboxylic Acid → 1-Benzyl 4-tert-butyl piperidine-1,4-dicarboxylate

HRID 906043Notes

Reaction equation

HRID 906043 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]([OH:19])=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NC(=NC(C)C)[O-])(C)C.C(NC(=NC(C)C)O[C:36]([CH3:39])([CH3:38])[CH3:37])(C)C>C(Cl)Cl>[N:11]1([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:12][CH2:13][CH:14]([C:17]([O:19][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:18])[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 7364891-Carbobenzoxy-4-piperidinecarboxylic AcidHCID 110417822-tert-Butyl-1,3-diisopropylisoureaHCID 20470589N,N'-diisopropylimidocarbamate

Product 1

HCID 15126991-Benzyl 4-tert-butyl piperidine-1,4-dicarboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[(benzyloxy)carbonyl]piperidine-4-carboxylic acid in DCM (0.2 M), 3 eq of tert-butyl. N,N′-diisopropylimidocarbamate were added and the mixture was stirred at RT. After 30 min, a further 1.5 eq of tert-butyl N,N′-diisopropylimidocarbamate were added and the solution stirred for an additional hour. The solution was filtered through a pad of celite and then through a pad of silica gel to give the product (83%); MS (ES+) m/z 320 (M+H)+

Workup

  1. stirringthe solution stirred for an additional hour
  2. filtrationThe solution was filtered through a pad of celite

Sources & evidence

ORD record
ord-3d0767596fe74ccf89e298da1912b148
Source dataset
uspto-grants-2011_09
Patent number
US08012982B2

Reaction notes

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