Hydrogen chloride-ethyl acetate → Benzyl benzyl[cis(+/-)-3-methoxypiperidin-4-yl]carbamate

HRID 43969Notes

Reaction equation

HRID 43969 reaction equation
Cl.C(OCC)(=O)C.[CH2:8]([N:15]([C:31]([O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:32])[C@H:16]1[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][C@H:17]1[O:29][CH3:30])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CO>[CH2:8]([N:15]([C@H:16]1[CH2:21][CH2:20][NH:19][CH2:18][C@H:17]1[O:29][CH3:30])[C:31](=[O:32])[O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 86648850tert-Butyl cis(+/-)-4-{benzyl[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate

Product 1

HCID 86712358Benzyl benzyl[cis(+/-)-3-methoxypiperidin-4-yl]carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 4 N hydrochloric acid/ethyl acetate solution (5 ml, 20 mmol) was added to a solution of tert-butyl cis(±)-4-{benzyl[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate obtained in Example (259b) (about 1.44 mmol) in methanol (1 mL). The mixture was stirred for one hour and the solvent was evaporated under reduced pressure. The reaction solution was diluted with ethyl acetate, washed with aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting compound was used for the next reaction without purification.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionThe reaction solution was diluted with ethyl acetate
  3. washwashed with aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting compound was used for the next reaction without purification

Sources & evidence

ORD record
ord-8c53541dcea1496f87d3bb6c2433f89e
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

Loading…