2-(Phenylmethyl)oxirane → HCID 178521329, compound

HRID 634772Notes

Reaction equation

HRID 634772 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([NH2:21])[CH2:17][CH2:16]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:22]1[CH2:31][CH:23]1[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]2[CH2:20][CH2:19][C@H:18]([NH:21][CH2:31][CH:23]([OH:22])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:17][CH2:16]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C@H:15]2[CH2:20][CH2:19][C@H:18]([NH:21][CH2:31][CH:23]([OH:22])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:17][CH2:16]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 948262-(Phenylmethyl)oxirane2×HCID 178511501HCID 178511501, compound

Product 2

HCID 178521329HCID 178521329, compoundHCID 178521330HCID 178521330, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of cis and trans 4-(4-benzyloxy-phenyl)-cyclohexyl-amine (preparation see under 43a, 1.0 g, 3.55 mmol), MeOH (100 ml) and 2,3-epoxypropyl-benzene (480 mg, 3.55 mmol) was refluxed for 3 days. Another portion of and 2,3-epoxypropyl-benzene (480 mg, 3.55 mmol) was added and stirring was continued for 2 days. The solvent was evaporated and the residue was purified by chromatography (SiO2, AcOEt-hexane 1:1) to give (RS)-1-[cis-4-(4-benzyloxy-phenyl)-cyclohexylamino]-3-phenyl-propan-2-ol (430 mg, colorless oil, MS: m/e=416.3 (M+H+)) and (RS)-1-[trans-4-(4-benzyloxy-phenyl)-cyclohexylamino]-3-phenyl-propan-2-ol (85 mg, white crystals, Mp. 137.5-138, MS: m/e=416.3 (M+H+)).

Workup

  1. temperaturewas refluxed for 3 days
  2. customThe solvent was evaporated
  3. customthe residue was purified by chromatography (SiO2, AcOEt-hexane 1:1)

Sources & evidence

ORD record
ord-0ab06fb86f794988834ef5a9356bf751
Source dataset
uspto-grants-2001_02
Patent number
US06184236B2

Reaction notes

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