Boron Trichloride → Raloxifene Bismethyl Ether (hydrochloride)

HRID 989803

Reaction equation

HRID 989803 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-1e25909ca3c341a2bdb0cddc8aeb31ff
Source dataset
uspto-grants-2002_10
Patent number
US06458811B1

Linked notes

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