Hydrochloric Acid → (R)-4-((5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-methylpiperidine

HRID 921162Notes

Reaction equation

HRID 921162 reaction equation
[Si:1]([O:18][C@H:19]([CH3:39])[CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1([CH3:38])[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCOCC1>[Si:1]([O:18][C@H:19]([CH3:39])[CH2:20][CH2:21][CH2:22][CH2:23][O:24][C:25]1([CH3:38])[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 123285187(R)-tert-butyl 4-((5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-methylpiperidine-1-carboxylate

Product 1

HCID 123395765(R)-4-((5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-methylpiperidineYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of (R)-tert-butyl 4-((5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-methylpiperidine-1-carboxylate (8.2 g, 14.81 mmol) and 4M HCl (22.21 mL, 89 mmol) in dioxane in 1,4-Dioxane (5 mL) was stirred at room temp for 2 h. Mixture was then concentrated, diluted with ethyl acetate (100 mL), washed with 1N NaOH, dried (Na2SO4), filtered and concentrated to afford (R)-4-((5-((tert-butyldiphenylsilyl)oxy)hexyl)oxy)-4-methylpiperidine (6.35 g, 14.00 mmol, 95% yield) as viscous oil. 1H NMR (500 MHz, CDCl3) δ 7.72-7.65 (m, 4H), 7.47-7.34 (m, 6H), 3.87 (sxt, J=5.9 Hz, 1H), 3.24 (t, J=6.4 Hz, 2H), 2.94-2.86 (m, 2H), 2.77-2.69 (m, 2H), 1.74-1.68 (m, 4H), 1.48-1.32 (m, 6H), 1.14 (s, 3H), 1.10-1.05 (m, 12H). LCMS (M+H)=454.2.

Workup

  1. concentrationMixture was then concentrated
  2. additiondiluted with ethyl acetate (100 mL)
  3. washwashed with 1N NaOH
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1e7595b26208424095bed68496c2c3e8
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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