Boron Trichloride → HCID 67089985, compound

HRID 2074423Notes

Reaction equation

HRID 2074423 reaction equation
C([O:4][C:5]1[C:14]([CH3:15])=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][C@@H:8]([CH:19]1[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:21][CH2:20]1)[O:9][C@H:10]2[CH2:16][NH:17][CH3:18])(C)C.B(Cl)(Cl)[Cl:34]>ClCCl>[ClH:34].[ClH:34].[CH3:15][C:14]1[CH:13]=[CH:12][C:11]2[C@H:10]([CH2:16][NH:17][CH3:18])[O:9][C@H:8]([CH:19]3[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:23][CH2:24]3)[CH2:7][C:6]=2[C:5]=1[OH:4]

Participants

4

Reactant 2

HCID 25135Boron TrichlorideHCID 67090221HCID 67090221, compound

Product 1

HCID 67089985HCID 67089985, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

Cool a solution of (1R,3S) [5-Isopropoxy-6-methyl-3-(1-phenethyl-piperidin-4-yl)-isochroman-1-ylmethyl]-methyl-amine in anhydrous dichloromethane (4 mL) to −20° C., and add 6 equivalents of BCl3 (using 1M BCl3 in dichloromethane) slowly into the solution. Following complete addition, stir the reaction mixture at −20° C. for 2 hours and 0° C. for 1 hour. Cool again to −20° C. and quench with anhydrous CH3OH (0.5 mL). Allow the resulting solution to warm to room temperature and concentrate. Purify the crude product on a 2 g SCX column and then by chromatography on a 1 g silica gel column (eluted by 7N NH3 in methanol:ethyl acetate=1:10). Collect and concentrate the appropriate fractions and treat with 2M HCl in diethyl ether to obtain the title compound. CIMS 395.4 (MH+), tR (min)=2.17.

Workup

  1. additionaddition
  2. wait0° C. for 1 hour
  3. temperatureCool again to −20° C.
  4. customquench with anhydrous CH3OH (0.5 mL)
  5. temperatureto warm to room temperature
  6. concentrationconcentrate
  7. customPurify the crude product on a 2 g SCX column
  8. washby chromatography on a 1 g silica gel column (eluted by 7N NH3 in methanol:ethyl acetate=1:10)
  9. customCollect
  10. concentrationconcentrate the appropriate fractions
  11. additiontreat with 2M HCl in diethyl ether

Sources & evidence

ORD record
ord-1deeac9a996f4e1eb87473f824a05844
Source dataset
uspto-grants-2011_04
Patent number
US07919508B2

Reaction notes

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