Acetonitrile → Benzyl 2-[4-(tert-butoxycarbonylamino)piperidin-1-yl]ethylcarbamate

HRID 656957

Reaction equation

HRID 656957 reaction equation
Br[CH2:2][CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>CN(C=O)C>[C:8]1([CH2:7][O:6][C:5]([NH:4][CH2:3][CH2:2][N:15]2[CH2:16][CH2:17][CH:18]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27])[CH2:19][CH2:20]2)=[O:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 278694benzyl N-(2-bromoethyl)carbamate2×HCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 22989976Benzyl 2-[4-(tert-butoxycarbonylamino)piperidin-1-yl]ethylcarbamateYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of phenylmethyl (2-bromoethyl)carbamate (12.9 g, 50 mmol) (prepared from phenylmethyl (2-bromoethyl)carbamate and phenylmethyl chloridocarbonate according to the method of A. J. Brouwer and R. M. J. Liskamp, European Journal of Organic Chemistry (2005), (3), 487-495), 1,1-dimethylethyl 4-piperidinylcarbamate (10 g, 50 mmol), potassium carbonate (6.9 g, 50 mmol), acetonitrile (100 ml) and DMF (30 ml) was heated at 40° C. for 2.5 days. The solvents were decanted from inorganic residues and evaporated. The residue was partitioned between ethyl acetate and dilute brine. The organic extract was dried (MgSO4) and evaporated affording a white solid (17.6 g, 93%).

Workup

  1. customThe solvents were decanted from inorganic residues
  2. customevaporated
  3. customThe residue was partitioned between ethyl acetate and dilute brine
  4. extractionThe organic extract
  5. dry with materialwas dried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-2be4e431668143509c580027eb637861
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Linked notes

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