Benzyl 4-tert-butoxycarbonylmethoxy-[1,4']bipiperidinyl-1'-carboxylate → Tert-butyl([1,4']bipiperidinyl-4-yloxy)-acetate

HRID 2106514Notes

Reaction equation

HRID 2106514 reaction equation
[C:1]([O:5][C:6]([CH2:8][O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH:16]2[CH2:21][CH2:20][N:19](C(OCC3C=CC=CC=3)=O)[CH2:18][CH2:17]2)[CH2:12][CH2:11]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:7])[CH2:8][O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH:16]2[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]2)[CH2:12][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 66941898Benzyl 4-tert-butoxycarbonylmethoxy-[1,4']bipiperidinyl-1'-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 86261192Tert-butyl([1,4']bipiperidinyl-4-yloxy)-acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 3.08 g (7.12 mmol) benzyl 4-tert-butoxycarbonylmethoxy-[1,4′]bipiperidinyl-1′-carboxylate and 300 mg 10% Pd/C in 60 mL MeOH was hydrogenated for 2 h at 50° C. and 3447 hPa hydrogen pressure. The catalyst was removed by suction filtering and the filtrate was evaporated to dryness. The product was reacted further without purification.

Workup

  1. customThe catalyst was removed by suction
  2. filtrationfiltering
  3. customthe filtrate was evaporated to dryness
  4. customThe product was reacted further without purification

Sources & evidence

ORD record
ord-ffe579903ba44abd93705bfa6478e723
Source dataset
uspto-grants-2009_08
Patent number
US07579341B2

Reaction notes

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