HCID 21103799, compound → (3R,5R)-5-((tert-Butyldimethylsilyl)oxy)piperidin-3-ol

HRID 1354845Notes

Reaction equation

HRID 1354845 reaction equation
[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][C@H:7]1[CH2:12][N:11](CC2C=CC(OC)=CC=2)[CH2:10][C@@H:9]([OH:22])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][C@H:7]1[CH2:12][NH:11][CH2:10][C@H:9]([OH:22])[CH2:8]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 21103799HCID 21103799, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21103800(3R,5R)-5-((tert-Butyldimethylsilyl)oxy)piperidin-3-olYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 329 (25.5 mmol) and 10% Pd/C (1 mol %) in MeOH (250 mL) was fitted with a balloon of hydrogen and allowed to stir at room temperature for 4 h. At that time, a vacuum was applied to remove any remaining hydrogen, the vessel was purged with nitrogen, diluted with MeOH (100 mL) and filtered through a pad of Celite on a fritted funnel. The resulting solution was concentrated to give 5-(R)-(tert-Butyl-dimethyl-silanyloxy)-piperidin-3-(R)-ol (330) as a colorless oil (25.0 mmol, 98% yield). 1H NMR (400 MHz, CD3OD) δ=0.13 ppm (s, 3H), 0.14 (s, 3H), 0.929 (s, 9H), 1.84 (br t, 2H, J=5 Hz), 2.71–2.78 (m, 2H), 2.97–3.05 (m, 2H), 4.04–4.09 (m, 1H), 4.19–4.24 (m, 1H).

Workup

  1. customto remove any remaining hydrogen
  2. customthe vessel was purged with nitrogen
  3. additiondiluted with MeOH (100 mL)
  4. filtrationfiltered through a pad of Celite on a fritted funnel
  5. concentrationThe resulting solution was concentrated

Sources & evidence

ORD record
ord-9ae0c3cb020844a0b94b6b327f582d6e
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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