Boron Trichloride → Raloxifene Bismethyl Ether (hydrochloride)

HRID 1007855Notes

Reaction equation

HRID 1007855 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 3 (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-bc66d1face444798b8df3d06c2213159
Source dataset
uspto-grants-2004_09
Patent number
US06797719B2

Reaction notes

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