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

HRID 730642Notes

Reaction equation

HRID 730642 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]>[N:13]1([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[CH2:12][CH2:11][CH:10]([O:9][CH2:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:15][CH2:14]1

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

Workup

  1. customwas hydrogenated at 50° C.
  2. customThe catalyst was removed by suction
  3. filtrationfiltering
  4. customthe filtrate was evaporated to dryness
  5. customThe oil remaining was reacted further without purification

Sources & evidence

ORD record
ord-f06395ffb5f348c78cc815568ae6f367
Source dataset
uspto-grants-2009_09
Patent number
US07582625B2

Reaction notes

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