Triethylamine → Benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate

HRID 1970462Notes

Reaction equation

HRID 1970462 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>CN(C1C=CN=CC=1)C.ClCCl>[CH2:26]([O:25][C:23]([N:11]1[CH2:12][CH2:13][CH:8]([NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:14])[CH2:9][CH2:10]1)=[O:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 21981786Benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4.94 g piperidin-4-yl-carbamic acid tert-butyl ester, 300 mg DMAP and 5.2 ml triethylamine in 50 ml dichloromethane were added 6.3 ml benzyl chloroformate dropwise at 0° C. After 8 h the suspension was diluted with dichloromethane and washed with half-saturated NaHCO3 and 0.1 M HCl. The crude product obtained after evaporation of the solvent was suspended in heptane, the supernatant solution being decanted yielding the product as colorless solid. Yield: 7.9 g.

Workup

  1. washwashed with half-saturated NaHCO3 and 0.1 M HCl
  2. customThe crude product obtained
  3. customafter evaporation of the solvent
  4. customthe supernatant solution being decanted

Sources & evidence

ORD record
ord-9dbb67c8ba4641c5860a3275310a3376
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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