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

HRID 1920182Notes

Reaction equation

HRID 1920182 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 acetate 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 acetate
  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-bdb60825c0df41b0b7f94f6d8023648e
Source dataset
uspto-grants-2012_05
Patent number
US08168794B2

Reaction notes

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