Triethylamine → 4-Butoxycarbonylamino-piperidine-1-carboxylic acid benzyl ester

HRID 1970464Notes

Reaction equation

HRID 1970464 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH2:17])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH2:25]([O:29][C:30](Cl)=[O:31])[CH2:26][CH2:27][CH3:28]>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:30]([O:29][CH2:25][CH2:26][CH2:27][CH3:28])=[O:31])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61140Butyl chloroformateHCID 178466404-Amino-1-N-Cbz-piperidine

Product 1

HCID 668559504-Butoxycarbonylamino-piperidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4.4 g 4-amino-piperidine-1-carboxylic acid benzyl ester hydrotrifluoroacetate and 5.3 ml triethylamine in 100 ml dichloromethane were added 1.8 ml butylchloroformate dropwise at 0° C. The suspension was stirred for 12 h, diluted with dichloromethane and washed with 0.1 M HCl and aqueous NaHCO3. The crude product was purified by flash chromatography on silica using ethyl acetate/heptan 1:2 as eluent.

Workup

  1. washwashed with 0.1 M HCl and aqueous NaHCO3
  2. customThe crude product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-fdb717f312624ba687c96eb59364e597
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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