(2R)-4-(2,3-Dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-({[(1R)-1-phenylethyl]amino}methyl)-2-pentanol → (2R)-2-(Aminomethyl)-4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-pentanol

HRID 418781Notes

Reaction equation

HRID 418781 reaction equation
[O:1]1[C:5]2[C:6]([C:10]([CH3:29])([CH3:28])[CH2:11][C@:12]([CH2:18][NH:19][C@@H](C3C=CC=CC=3)C)([OH:17])[C:13]([F:16])([F:15])[F:14])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1>CCO.[Pd]>[NH2:19][CH2:18][C@:12]([OH:17])([CH2:11][C:10]([C:6]1[C:5]2[O:1][CH2:2][CH2:3][C:4]=2[CH:9]=[CH:8][CH:7]=1)([CH3:29])[CH3:28])[C:13]([F:15])([F:16])[F:14]

Participants

4

Reactant 1

HCID 66648706(2R)-4-(2,3-Dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-({[(1R)-1-phenylethyl]amino}methyl)-2-pentanol

Product 1

HCID 57615952(2R)-2-(Aminomethyl)-4-(2,3-dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-pentanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(2R)-4-(2,3-Dihydro-1-benzofuran-7-yl)-1,1,1-trifluoro-4-methyl-2-({[(1R)-1-phenylethyl]amino}methyl)-2-pentanol (Intermediate 23, (480 mg, 1.178 mmol) was dissolved in EtOH (13 mL) and hydrogenated over 10% palladium on charcoal (119 mg) at 50 psi and room temperature for 5 hours. Catalyst was removed by filtration through a microfibre filter pad and Celite. The Celite was washed several times with EtOH. The filtrate was evaporated in vacuo to give the title compound as a pale grey solid (330 mg).

Workup

  1. customCatalyst was removed by filtration through a microfibre filter pad and Celite
  2. washThe Celite was washed several times with EtOH
  3. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-211844ac30ca418d9bcb750cbaf07243
Source dataset
uspto-grants-2012_01
Patent number
US08093281B2

Reaction notes

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