HCID 59200382, compound → HCID 59200356, compound

HRID 1685297Notes

Reaction equation

HRID 1685297 reaction equation
[C:1]1([C@@:7]([OH:21])([CH2:18][CH2:19][CH3:20])[CH2:8][NH:9][C@H](C2C=CC=CC=2)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CCO.[OH-].[OH-].[Pd+2]>[NH2:9][CH2:8][C@:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([OH:21])[CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 1

HCID 59200382HCID 59200382, compound

Product 1

HCID 59200356HCID 59200356, compoundYield 100.8%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of (25)-2-phenyl-1-{[(1S)-1-phenylethyl]amino}pentan-2-ol (0.954 g, 3.37 mmol) in EtOH (34 mL) was added Pd(OH)2/C (10%, 644 mg), then stirred at room temperature under 1 atmosphere of H2 overnight. The reaction was filtered through Celite, washed with EtOH, and the filtrate was concentrated to afford the desired product (609 mg, 100%) as an oil: 1H NMR (400 MHz, CDCl3) δ ppm 7.35-7.40 (2H, m), 7.32 (2H, t, J=7.71 Hz), 7.21 (1H, t, J=7.20 Hz), 3.10 (1H, d, J=12.38 Hz), 2.86 (1H, d, J=12.63 Hz), 2.58 (3H, s), 1.65-1.76 (2H, m), 1.28-1.39 (1H, m), 0.96-1.07 (1H, m), 0.82 (3H, t, J=7.33 Hz); [α]D20° C.=+4.2° (c=1, EtOH).

Workup

  1. filtrationThe reaction was filtered through Celite
  2. washwashed with EtOH
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c34cc5f16a3245ae9f974d7f99458895
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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