Boron Trichloride → Raloxifene Bismethyl Ether (hydrochloride)

HRID 2185116Notes

Reaction equation

HRID 2185116 reaction equation
B(Cl)(Cl)[Cl:2].[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]([C:15](=[O:31])[C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:18][CH:17]=3)=[C:13]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[S:12][C:11]=2[CH:40]=1>C(Cl)Cl>[ClH:2].[CH3:5][O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]([C:15](=[O:31])[C:16]3[CH:17]=[CH:18][C:19]([O:22][CH2:23][CH2:24][N:25]4[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]4)=[CH:20][CH:21]=3)=[C:13]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=3)[S:12][C:11]=2[CH:40]=1

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 10767755Raloxifene Bismethyl Ether

Product 1

HCID 45260096Raloxifene Bismethyl Ether (hydrochloride)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22.5 °C

Procedure

A mixture of the compound prepared as described in Preparation 1 (8.46 grams) and the acid chloride prepared as described in Preparation 4 (10.0 grams) in methylene chloride (350 mL) was cooled to about 20-25° C. The cool mixture was treated with boron trichloride (2.6 mL), and the resulting mixture mechanically stirred. The reaction was monitored by HPLC using the assay described above. After 85 minutes, the in situ HPLC yield based on a 6-methoxy-2-(4-methoxyphenyl)-3-[4-(2-piperidinoethoxy)benzoyl]benzo[b]thiophene standard was 88%.

Workup

  1. additionA mixture of the compound
  2. customprepared
  3. customthe in situ HPLC yield

Sources & evidence

ORD record
ord-22653c533f1d43f3924170a22f7ae830
Source dataset
uspto-grants-2002_06
Patent number
US06399778B1

Reaction notes

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