HCID 69329986, compound → HCID 69330611, compound

HRID 2299676Notes

Reaction equation

HRID 2299676 reaction equation
Cl.C([N:9]([CH2:23][C@H:24]([OH:33])[CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:10]1[CH2:16][CH2:15][CH2:14][C:13]2[CH:17]=[C:18]([OH:22])[C:19]([Cl:21])=[CH:20][C:12]=2[CH2:11]1)C1C=CC=CC=1.[H][H]>ClC1C=CC=CC=1.CO.[Pd]>[ClH:21].[Cl:21][C:19]1[C:18]([OH:22])=[CH:17][C:13]2[CH2:14][CH2:15][CH2:16][CH:10]([NH:9][CH2:23][C@H:24]([OH:33])[CH2:25][O:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:11][C:12]=2[CH:20]=1

Participants

6

Reactant 2

HCID 69329986HCID 69329986, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69330611HCID 69330611, compoundYield 150%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 7964ChlorobenzeneSolvent

Procedure

A mixture of (2S)-1-[N-benzyl-N-(3-chloro-6,7,8,9-tetrahydro-2-hydroxy-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol hydrochloride (121 mg) and 10% Pd/C (50% wet, 18 mg) in chlorobenzene (1.8 ml) and MeOH (0.4 ml) was stirred at room temperature in the presence of hydrogen at an atmospheric pressure for 1 hour and filtered. The filtrate was evaporated in vacuo, and the residue was partitioned between ethyl acetate and a saturated aqueous solution of sodium bicarbonate. The organic layer was separated, washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was chromatographed (dichloromethane-methanol) over silica gel (2.0 g). The eluate was treated with 4N hydrogen chloride in ethyl acetate and evaporated in vacuo. The residue was triturated in diisopropyl ether, and the precipitated powder was collected by filtration to afford (2S)-1-(3-chloro-6,7,8,9-tetrahydro-2-hydroxy-5-H-benzocyclohepten-6-yl)amino-3-phenoxy-2-propanol hydrochloride (74 mg, 75%) as a colorless powder.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue was partitioned between ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was chromatographed (dichloromethane-methanol) over silica gel (2.0 g)
  9. additionThe eluate was treated with 4N hydrogen chloride in ethyl acetate
  10. customevaporated in vacuo
  11. customThe residue was triturated in diisopropyl ether
  12. filtrationthe precipitated powder was collected by filtration

Sources & evidence

ORD record
ord-0855004c64f24f5c92f88a76c423fc14
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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