Triethylamine → racemic trans-2-[1-(2-chlorophenyl)-2-(4-methoxyphenyl)-1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridin-5-yl]cyclohexanol

HRID 1790036Notes

Reaction equation

HRID 1790036 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[CH2:15][CH2:14][NH:13][CH2:12][C:11]=2[CH:10]=[C:9]1[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.[CH:25]12[O:31][CH:26]1[CH2:27][CH2:28][CH2:29][CH2:30]2.C(N(CC)CC)C>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:16]2[CH2:15][CH2:14][N:13]([C@@H:25]3[CH2:30][CH2:29][CH2:28][CH2:27][C@H:26]3[OH:31])[CH2:12][C:11]=2[CH:10]=[C:9]1[C:17]1[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9246Cyclohexene oxideHCID 220385001-(2-chlorophenyl)-2-(4-methoxyphenyl)4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 69664110racemic trans-2-[1-(2-chlorophenyl)-2-(4-methoxyphenyl)-1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridin-5-yl]cyclohexanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(2-chlorophenyl)-2-(4-methoxyphenyl)-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine (Example 2, 500 mg, 1.33 mmol), cyclohexene oxide (1.34 mL, 13.3 mmol), and trietylamine (0.55 mL, 3.99 mmol) in ethanol (14 mL) was heated at reflux for 20 h. The solution was cooled to rt, and evaporated. The residue was purified by silica gel column, eluting with 3:1 to 2:1 hexanes:ethyl acetate. The product, racemic trans-2-[1-(2-chlorophenyl)-2-(4-methoxyphenyl)-1,4,6,7-tetrahydro-5H-pyrrolo[3,2-c]pyridin-5-yl]cyclohexanol, was isolated as a pale yellow solid (398 mg, 63%). LC-MS m/z (MH+) 437.1, retention time 2.45 min (method 1).

Workup

  1. temperatureat reflux for 20 h
  2. customevaporated
  3. customThe residue was purified by silica gel column
  4. washeluting with 3:1 to 2:1 hexanes

Sources & evidence

ORD record
ord-293f4bd587b248f481c424a748897cdb
Source dataset
uspto-grants-2006_07
Patent number
US07071207B2

Reaction notes

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