Triethylamine → Tert-butyl-dimethyl-(3-piperidylmethoxy)silane

HRID 1427115Notes

Reaction equation

HRID 1427115 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][OH:8])[CH2:2]1.C(N(CC)CC)C.[C:16]([Si:20]([CH3:23])([CH3:22])Cl)([CH3:19])([CH3:18])[CH3:17]>C(Cl)Cl>[C:16]([Si:20]([CH3:23])([CH3:22])[O:8][CH2:7][CH:3]1[CH2:4][CH2:5][CH2:6][NH:1][CH2:2]1)([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 107308Piperidin-3-ylmethanol

Product 1

HCID 58992622Tert-butyl-dimethyl-(3-piperidylmethoxy)silaneYield 60.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of piperidin-3-ylmethanol (2.10 g, 0.018 mol) in CH2Cl2 (20 mL) is added triethylamine (5.53 g, 0.0547 mol) followed by t-butyldimethylchlorosilane (4.127 g, 0.0275 mol) and the reaction mixture is stirred at room temperature. After 24 hours, the reaction mixture is washed with water, saturated solution of NaHCO3, and brine. The combined organic layers are dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (silica gel) over a gradient using 0-10% MeOH in dichloromethane to afford the title compound (2.50 g, 60%). Mass spectrum (m/z): 231.2 (M+1).

Workup

  1. washthe reaction mixture is washed with water, saturated solution of NaHCO3, and brine
  2. dry with materialThe combined organic layers are dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by flash chromatography (silica gel) over a gradient

Sources & evidence

ORD record
ord-fa4cdf0619044defa4131b55f83d0cb8
Source dataset
uspto-grants-2015_01
Patent number
US08933098B2

Reaction notes

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