Ethyl Acetate → HCID 68912483, compound

HRID 732723Notes

Reaction equation

HRID 732723 reaction equation
C(OCC)(=O)C.[C:7]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=O)[CH2:12][CH2:11]1)(=[O:9])[CH3:8].[Cl:19]C(OCC)=O.[C:25]1([C@H:35]([N:37]([CH2:45][CH:46]2[CH:50]([C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)[CH2:49][NH:48][CH2:47]2)C(=O)OC(C)(C)C)[CH3:36])[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][CH:26]=1>O.C(N(CC)CC)C>[ClH:19].[C:7]([N:10]1[CH2:11][CH2:12][CH:13]([C:16]([N:48]2[CH2:49][CH:50]([C:51]3[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=3)[CH:46]([CH2:45][NH:37][C@@H:35]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)[CH3:36])[CH2:47]2)=[O:18])[CH2:14][CH2:15]1)(=[O:9])[CH3:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 10928Ethyl chloroformateHCID 1172551-Acetylpiperidine-4-carboxylic acidHCID 86628564HCID 86628564, compound

Product 1

HCID 68912483HCID 68912483, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

An 8.0 ml ethyl acetate solution of 318 mg of 1-acetylpiperidine-4-carboxylic acid was mixed with 0.18 ml of ethyl chloroformate, 0.52 ml of triethylamine and 400 mg of tert-butyl [(1R)-1-(1-naphthyl)ethyl][(4-phenylpyrrolidin-3-yl)methyl]carbamate in that order and stirred at room temperature for 30 minutes. This was mixed with 10 ml of water and extracted with ethyl acetate. The solvent was evaporated, and the thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol). This was treated with 4 M hydrogen chloride/ethyl acetate and concentrated to dryness to obtain 75 mg of (1R)—N-({1-[(1-acetylpiperidin-4-yl)carbonyl]-4-phenylpyrrolidin-3-yl}methyl)-1-(1-naphthyl)ethanamine hydrochloride as a pale pink solid.

Workup

  1. extractionextracted with ethyl acetate
  2. customThe solvent was evaporated
  3. customthe thus obtained residue was purified by a silica gel column chromatography (chloroform-methanol)
  4. additionThis was treated with 4 M hydrogen chloride/ethyl acetate
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-b9301001efa640a08e761fdc40a889f3
Source dataset
uspto-grants-2009_09
Patent number
US07585886B2

Reaction notes

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