2-(4-Chlorophenoxymethyl)-4-benzyloxy-1-[3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl]-benzimidazole → (RS) 2-(4-chlorophenoxymethyl)-4hydroxy-1-[3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl]benzimidazole

HRID 1383992Notes

Reaction equation

HRID 1383992 reaction equation
[Cl:1][C:2]1[CH:42]=[CH:41][C:5]([O:6][CH2:7][C:8]2[N:12]([CH2:13][CH2:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]3)[C:11]3[CH:29]=[CH:30][CH:31]=[C:32]([O:33]CC4C=CC=CC=4)[C:10]=3[N:9]=2)=[CH:4][CH:3]=1>C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C:8]2[N:12]([CH2:13][CH2:14][CH2:15][CH:16]3[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]3)[C:11]3[CH:29]=[CH:30][CH:31]=[C:32]([OH:33])[C:10]=3[N:9]=2)=[CH:41][CH:42]=1

Participants

4

Reactant 1

HCID 211884842-(4-Chlorophenoxymethyl)-4-benzyloxy-1-[3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl]-benzimidazole

Product 1

HCID 21188576(RS) 2-(4-chlorophenoxymethyl)-4hydroxy-1-[3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl]benzimidazoleYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (RS) 2-(4-chlorophenoxymethyl)-4-benzyloxy-1-[3-[1-(t-butoxycarbonyl)piperidin-3-yl]propyl]-benzimidazole (245 mg, 0.42 mmol, 1.0 eq) in ethyl acetate (4.2 ml) was degassed and then treated with 5% palladium on carbon (250 mg). The resulting mixture was stirred under a hydrogen atmosphere. The reaction mixture was then filtered through a CELITE™ cake layer. The catalyst was washed thoroughly with ethyl acetate and ethanol. The filtrate was condensed on a rotoevaporator to yield the desired title product in 78% yield.

Workup

  1. filtrationThe reaction mixture was then filtered through a CELITE™ cake layer
  2. washThe catalyst was washed thoroughly with ethyl acetate and ethanol
  3. customcondensed on a rotoevaporator

Sources & evidence

ORD record
ord-fc018d48ef794f65ab2382653a731236
Source dataset
uspto-grants-2001_07
Patent number
US06255494B1

Reaction notes

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