HCID 57588941, compound → 4-((Tert-butyldimethylsilyl)oxy)piperidine

HRID 1808742Notes

Reaction equation

HRID 1808742 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].CO>[Si:15]([O:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

5

Reactant 2

HCID 57588941HCID 57588941, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 114813284-((Tert-butyldimethylsilyl)oxy)piperidine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a methanol (28 mL) solution of 1-benzyl-4-{[tert-butyl(dimethyl)silyl]oxy}piperidine (2.80 g, 9.18 mmol) was added palladium hydroxide on carbon (20 weight %, 280 mg. 0.40 mmol) and stirred under an atmospheric pressure of hydrogen for 16 hours. The reaction mixture was filtered through diatomaceous earth and washed with methanol. The filtrate was concentrated in vacuo to afford the title compound. This crude product was used in the subsequent step without further purification. 1H NMR (500 MHz, CDCl3) δ 3.77-3.70 (m, 1H), 3.09-3.02 (m, 2H), 2.61 (ddd, J=12.5, 9.5, 3.0 Hz, 2H), 1.82-1.72 (m, 2H), 1.42 (dtd, J=13.0, 9.0, 3.7 Hz, 2H), 0.89 (s, 9H), 0.05 (s, 6H); LC-MS: m/z 216.2 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered through diatomaceous earth
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-fc717d15164e4b2b8eec45dbb2be8b3a
Source dataset
uspto-grants-2013_01
Patent number
US08361994B2

Reaction notes

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