Tecalcet → HCID 69709859, compound

HRID 322594Notes

Reaction equation

HRID 322594 reaction equation
[CH3:1][C@@H:2]([NH:11][CH2:12][CH2:13][CH2:14][C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9]C)[CH:4]=1>ClCCl>[ClH:21].[Cl:21][C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:14][CH2:13][CH2:12][NH:11][C@@H:2]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([OH:9])[CH:4]=1)[CH3:1]

Participants

3

Reactant 1

HCID 158797Tecalcet

Product 1

HCID 69709859HCID 69709859, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of NPS R-568 (30.3 g 100 mmol) in dichloromethane at −78° C. was treated dropwise with borontribromide (50 g, 200 mmol). The reaction 40 was stirred 1 hr at rt and poured over ice. The hydrobromide was extracted from the aqueous phase with chloroform. The chloroform solubles were then washed (4×100 ml) with 50% HCl. The chloroform wash was dried over anhydrous magnesium sulfate and concentrated to afford (R)-N-[3-(2-chlorophenyl)propyl]-1-(3-hydroxyphenyl)ethylamine hydrochloride as a solid. A solution of sodium hydride (0.48 g, 20 mmol) in dimethylformamide was treated with (R)-N-[3-(2-chlorophenyl)propyl]-1-(3-hydroxyphenyl)ethylamine hydrochloride (3.25 g, 10 mmol) and the reaction stirred 1 hr at rt. The reaction was treated with iodoethane (1.71 g, 11 mmol) and stirred 16 hr at rt. Work-up and chromatography through silica using 3% methanol in chloroform afforded (R)-N-[3-(2-chlorophenyl)propyl]-1-(3-ethoxyphenyl)ethylamine, 6T, as an oil; m/z (rel. int.) 316 (M+, 1), 302 (100), 282 (11), 196 (5), 178 (7), 149 (74), 121 (34), 103 (25), 91 (28), 77 (29).

Workup

  1. customThe reaction 40
  2. additionpoured over ice
  3. extractionThe hydrobromide was extracted from the aqueous phase with chloroform
  4. washThe chloroform solubles were then washed (4×100 ml) with 50% HCl
  5. washThe chloroform wash
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ab799db434444b53bd16fca8c78a9eb5
Source dataset
uspto-grants-2001_04
Patent number
US06211244B1

Reaction notes

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