Dichloromethane → HCID 68914189, compound

HRID 732681Notes

Reaction equation

HRID 732681 reaction equation
ClCCl.[I-].[C:5]([O:9][C:10]([N:12]([CH2:25][C@@H:26]1[C@@H:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:29][N:28]([C:37]([N:39]2[CH:43]=[CH:42][N+](C)=[CH:40]2)=[O:38])[CH2:27]1)[C@@H:13]([C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][CH:16]=1)[CH3:14])=[O:11])([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C.N1CC[CH:55]([C:58]([O:60][CH2:61][CH3:62])=[O:59])[CH2:54]C1>C(OCC)(=O)C>[C:5]([O:9][C:10]([N:12]([CH2:25][C@@H:26]1[C@@H:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:29][N:28]([C:37]([N:39]2[CH2:43][CH2:42][CH:55]([C:58]([O:60][CH2:61][CH3:62])=[O:59])[CH2:54][CH2:40]2)=[O:38])[CH2:27]1)[C@@H:13]([C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:22]=[CH:23][CH:24]=1)[CH3:14])=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylateHCID 86628547HCID 86628547, compound

Product 1

HCID 68914189HCID 68914189, compoundYield 56.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 6.0 ml dichloromethane solution of 250 mg of 1-{[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}-3-methyl-1H-imidazol-3-ium iodide and 31 mg of triethylamine was mixed with 48 mg of ethyl 4-piperidine-carboxylate and stirred overnight at room temperature. The reaction solution was mixed with ethyl acetate and washed with water. The solvent was evaporated under a reduced pressure, and the thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol) to obtain 106 mg of ethyl 1-{[(3R,4S)-3-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-4-phenylpyrrolidin-1-yl]carbonyl}piperidine-4-carboxylate as a white amorphous substance.

Workup

  1. washwashed with water
  2. customThe solvent was evaporated under a reduced pressure
  3. customthe thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-059a22fe0a5b427c8f3d939b130c20a1
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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