Benzylamine → Ethyl trans-3-hydroxy-4-[(phenylmethyl)amino]-1-piperidinecarboxylate

HRID 1088346Notes

Reaction equation

HRID 1088346 reaction equation
[CH:1]12[O:7][CH:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2]2.[C:13]1([CH2:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[OH:7][C@H:1]1[C@H:6]([NH:20][CH2:19][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2]1.[OH:7][C@@H:6]1[CH2:5][CH2:4][N:3]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:2][C@H:1]1[NH:20][CH2:19][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 12414163Ethyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate2×

Product 2

HCID 13677850Ethyl trans-3-hydroxy-4-[(phenylmethyl)amino]-1-piperidinecarboxylateHCID 67312643Ethyl trans-4-hydroxy-3-[(phenylmethyl)amino]-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3.4 parts of ethyl 7-oxa-3-azabicyclo[4,1,0]heptane-3-carboxylate, 2.1 parts of benzenemethanamine and 40 parts of ethanol was stirred and refluxed for 17 hours. Another 0.3 parts of ethyl 7oxa-3-azabicyclo[4,1,0]heptane-3-carboxylate were added and stirring at reflux was continued for 4 hours. The reaction mixture was evaporated. The residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 3.4 parts (61.8%) of a mixture of ethyl trans-3-hydroxy-4-[(phenylmethyl)amino]-1-piperidinecarboxylate and ethyl trans-4-hydroxy-3-[(phenylmethyl)amino]-1- piperidinecarboxylate as an oily residue (intermediates 35 and 36).

Workup

  1. temperaturerefluxed for 17 hours
  2. stirringstirring
  3. temperatureat reflux
  4. customThe reaction mixture was evaporated
  5. customThe residue was purified by column-chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated

Sources & evidence

ORD record
ord-f251b6e8341e4766866a5e25efc511fa
Source dataset
uspto-grants-1990_10
Patent number
US04962115

Reaction notes

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