1,2-Dichloroethane → cis (+/-)-1-Benzyl 3-methyl 5-(tert-butoxycarbonylamino)piperidine-1,3-dicarboxylate

HRID 69985Notes

Reaction equation

HRID 69985 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][C@H:15]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C@H:13]([C:25]([OH:27])=[O:26])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[CH2:30](Cl)CCl.CN(C1C=CC=CN=1)C>ClCCl>[C:21]([O:20][C:18]([NH:17][C@H:15]1[CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[CH2:12][C@@H:13]([C:25]([O:27][CH3:30])=[O:26])[CH2:14]1)=[O:19])([CH3:23])([CH3:24])[CH3:22]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 887MethanolHCID 218852-DimethylaminopyridineHCID 86656441HCID 86656441, compound

Product 1

HCID 95731685cis (+/-)-1-Benzyl 3-methyl 5-(tert-butoxycarbonylamino)piperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cis (+/−)-1-(benzyloxycarbonyl)-5-(tert-butoxycarbonylamino)piperidine-3-carboxylic acid (1.0 eq), methanol (20 eq.) and EDC (1.3 eq) in dichloromethane at a concentration of 0.25 M at 0*C was added dimethylaminopyridine (0.1 eq). After stirring for 48 hours as the reaction was allowed to warm to rt the volatiles were removed in vacuo. Upon addition of ethyl actetate and washing with H2O (3×), 1N HCl, NaHCO3(sat.) and brine, the solution was dried over MgSO4, filtered, concentrated and purified by column chromatography (25% ethyl acetate/hexanes) to yield cis (+/−)-1-benzyl 3-methyl 5-(tert-butoxycarbonylamino)piperidine-1,3-dicarboxylate. LCMS (m/z): 293.1 (MH-Boc+); LC Rt=4.09 min

Workup

  1. customwere removed in vacuo
  2. additionUpon addition of ethyl actetate
  3. washwashing with H2O (3×), 1N HCl, NaHCO3(sat.) and brine
  4. dry with materialthe solution was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by column chromatography (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5f8ee3ba208640eeb64e5c54f50b0cf7
Source dataset
uspto-grants-2014_09
Patent number
US08822497B2

Reaction notes

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