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1,2-Dichloroethane → {2-Oxo-2-[3-(4-phenyl-piperidin-1-yl)-pyrrolidin-1-yl]-ethyl}-carbamic acid tert-butyl ester

HRID 406470
Notes
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Reaction equation

HRID 406470 reaction equation
Cl.Cl.[C:3]1([CH:9]2[CH2:14][CH2:13][N:12]([CH:15]3[CH2:19][CH2:18][NH:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:20]([O:24][C:25]([NH:27][CH2:28][C:29](O)=[O:30])=[O:26])([CH3:23])([CH3:22])[CH3:21].C(Cl)CCl.CCN(CC)CC>C(Cl)Cl>[C:20]([O:24][C:25](=[O:26])[NH:27][CH2:28][C:29](=[O:30])[N:17]1[CH2:18][CH2:19][CH:15]([N:12]2[CH2:11][CH2:10][CH:9]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH2:14][CH2:13]2)[CH2:16]1)([CH3:23])([CH3:21])[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 78288N-(tert-butoxycarbonyl)glycineHCID 688998884-Phenyl-1-pyrrolidin-3-yl-piperidine dihydrochloride

Product 1

HCID 59764640{2-Oxo-2-[3-(4-phenyl-piperidin-1-yl)-pyrrolidin-1-yl]-ethyl}-carbamic acid tert-butyl esterYield 38.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4-phenyl-1-pyrrolidin-3-yl-piperidine dihydrochloride (preparation #7) (3.0 g, 9.90 mmol), tert-butoxycarbonylamino-acetic acid (1.73 g, 9.90 mmol) and EDC (1.90, 9.90 mmol) in DCM (60 mL) was added Et3N (5.5 mL, 39.6 mmol). The reaction mixture was stirred at ambient temperature for about 16 h. DCM was added and the organic layer was washed with water and saturated NaHCO3, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography using 5% MeOH/EtOAc as the mobile phase to afford {2-oxo-2-[3-(4-phenyl-piperidin-1-yl)-pyrrolidin-1-yl]-ethyl}-carbamic acid tert-butyl ester (1.47 g, 38% yield). RP-HPLC (Table 1, Method b) Rt 1.54 min; m/z: (M+H)+ 388.

Workup

  1. washthe organic layer was washed with water and saturated NaHCO3
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f81ce7581c3949cf9775471b69c400aa
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08754107B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes