HCID 69584140, compound → 67323-60-8

HRID 2119830Notes

Reaction equation

HRID 2119830 reaction equation
[ClH:1].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@H:10]([NH:12][C@H](C)C2C=CC=CC=2)[CH3:11])=[CH:5][CH:4]=1>[Pd].CO>[ClH:1].[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C@H:10]([NH2:12])[CH3:11])=[CH:7][CH:8]=1

Participants

4

Reactant 1

HCID 69584140HCID 69584140, compound

Product 1

HCID 6662439267323-60-8Yield 73.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A hastalloy autoclave was charged with (2R)-1-(4-hydroxyphenyl)-2-(N-[(R)-a-methylbenzyl])amino propane hydrochloride (72.3 g, 248 mmol), 5% Pd/C (16.0 g, wetted with 100 mL of EtOH), and MeOH (400 mL). The autoclave was pressurized to 50 psi H2 and heated to 50° C. for 6 h with vigorous stirring. After cooling, purging with nitrogen and filtering the mixture, the filtrate was concentrated on a rotary evaporator under vacuum. The resulting oily foam was dissolved in a minimal amount of MeOH and was triturated by addition of EtOAc. The solid was filtered, and another crop of solid which precipitated from the filtrate was also collected. The combined solids were dried in a 45° C. vacuum oven overnight to yield 34.2 g (73%) of a white solid. MP 160° C. [dec]. MS(FD+) m/z 151 (92%).

Workup

  1. temperatureAfter cooling
  2. custompurging with nitrogen
  3. filtrationfiltering the mixture
  4. concentrationthe filtrate was concentrated on a rotary evaporator under vacuum
  5. dissolutionThe resulting oily foam was dissolved in a minimal amount of MeOH
  6. customwas triturated by addition of EtOAc
  7. filtrationThe solid was filtered
  8. customanother crop of solid which precipitated from the filtrate
  9. customwas also collected
  10. customThe combined solids were dried in a 45° C. vacuum oven overnight

Sources & evidence

ORD record
ord-436d9452f6384663a1406515c27a6284
Source dataset
uspto-grants-2004_02
Patent number
US06686372B2

Reaction notes

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