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[(3,4,5-Trimethoxyphenoxy)methyl]oxirane → 1-[2-Hydroxy-3-(3,4,5-trimethoxyphenyl)-propyl]-piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

HRID 1454127
Notes
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Reaction equation

HRID 1454127 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:39]=[C:40]([O:44][CH3:45])[C:41]=1[O:42][CH3:43])OCC1CO1>C(O)(C)C>[C:1]1([CH2:7][CH2:8][CH2:9][CH:10]([NH:20][C:21]([CH:23]2[CH2:28][CH2:27][N:26]([CH2:41][CH:31]([OH:30])[CH2:32][C:33]3[CH:39]=[C:40]([O:44][CH3:45])[C:41]([O:42][CH3:43])=[C:31]([O:30][CH3:29])[CH:32]=3)[CH2:25][CH2:24]2)=[O:22])[CH2:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 5743635[(3,4,5-Trimethoxyphenoxy)methyl]oxiraneHCID 12020260Piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide

Product 1

HCID 865855441-[2-Hydroxy-3-(3,4,5-trimethoxyphenyl)-propyl]-piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amideYield 121%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
70 °C

Procedure

Piperidine-4-carboxylic acid [4-phenyl-1-(3-phenyl-propyl)-butyl]-amide (4) (150.7 mg; 0.4 mmol) is dissolved in isopropanol (10 mL) at ambient temperature. (+/−)-2-(3,4,5-Trimethoxy-phenoxymethyl)-oxirane(95.2 mg; 0.4 mmol) is added, then the mixture is heated to 70° C. and maintained for 18 hours. After cooling to ambient temperature, the solution is concentrated in vacuo at 40° C. The residue is purified via silica gel chromatography with gradient elution (10%→100% acetone in hexanes) affording the desired product (145.9 mg) as an oil. ESMS: MH+ 619.4 (base).

Workup

  1. temperaturemaintained for 18 hours
  2. temperatureAfter cooling to ambient temperature
  3. concentrationthe solution is concentrated in vacuo at 40° C
  4. customThe residue is purified via silica gel chromatography with gradient elution (10%→100% acetone in hexanes)

Sources & evidence

ORD record
ord-b47e09edb5c340f985082418b963fd06
Source dataset
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07476680B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes