1-Benzyl-4-((6-((tert-butyldimethylsilyl)oxy)hexyl)oxy)piperidine → HCID 58505168, compound

HRID 1944858Notes

Reaction equation

HRID 1944858 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[Si:22]([O:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][CH:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

5

Reactant 2

HCID 575169301-Benzyl-4-((6-((tert-butyldimethylsilyl)oxy)hexyl)oxy)piperidineHCID 178418361HCID 178418361, compound

Product 1

HCID 58505168HCID 58505168, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Intermediate 22 (157 mg, 0.387 mmol) was dissolved in MeOH (5 mL) then added 10% (w/w) Pd/C (41 mg, 0.0387 mmol). The reaction vessel was attached to 3-way valve with balloon containing hydrogen gas. The vessel was evacuated 3 times then back flushed with hydrogen. The resulting suspension was stirred overnight, filtered, and concentrated to give the title compound (120 mg) as clear oil. The compound was used with no further purification. ES/MS calcd for C17H38NO2Si+ 316.3. Found m/z=316.3 (M+H)+.

Workup

  1. customThe reaction vessel was attached to 3-way valve with balloon
  2. customThe vessel was evacuated 3 times
  3. customthen back flushed with hydrogen
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3fbf310c0dfe43c58cab7d547eaeb997
Source dataset
uspto-grants-2013_03
Patent number
US08394829B2

Reaction notes

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