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

HRID 2267231Notes

Reaction equation

HRID 2267231 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-208cc8d96b0e4dc7a8ef42807b070d86
Source dataset
uspto-grants-2010_12
Patent number
US07858622B2

Reaction notes

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