Tetrahydrofuran → 1-(1-Propyl)oxy-2,2,6,6-tetramethyl-4-trimethylsilyloxypiperidine

HRID 1404316Notes

Reaction equation

HRID 1404316 reaction equation
[CH3:1][Si:2]([CH3:16])([CH3:15])[O:3][CH:4]1[CH2:9][C:8]([CH3:11])([CH3:10])[NH+:7]([O-:12])[C:6]([CH3:14])([CH3:13])[CH2:5]1.[CH2:17]1[CH2:21]OC[CH2:18]1>>[CH2:18]([O:12][N:7]1[C:6]([CH3:14])([CH3:13])[CH2:5][CH:4]([O:3][Si:2]([CH3:1])([CH3:15])[CH3:16])[CH2:9][C:8]1([CH3:10])[CH3:11])[CH2:17][CH3:21]

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 580038804-trimethylsilyloxy-2,2,6,6-tetramethylpiperidine-N-oxide

Product 1

HCID 683153531-(1-Propyl)oxy-2,2,6,6-tetramethyl-4-trimethylsilyloxypiperidine

Procedure

In another reaction vessel, 96.2 g (394 mmol) of 4-trimethylsilyloxy-2,2,6,6-tetramethylpiperidine-N-oxide was dissolved in 100 ml of dehydrated THF, and the Grignard reactant prepared was dropped at 0° C. After a reaction for 3 hours, the solution was concentrated by a rotary evaporator. 500 mL of water was added to the residue and an extraction was carried out using 500 mL in total of ethyl acetate, and the organic layer was concentrated by a rotary evaporator. The residue was purified by column chromatography (silica gel, hexane/ethyl acetate=20/1, volume ratio) to obtain 38.5 g of 1-(1-propyl)oxy-2,2,6,6-tetramethyl-4-trimethylsilyloxypiperidine.

Workup

  1. additionwas dropped at 0° C
  2. customAfter a reaction for 3 hours
  3. concentrationthe solution was concentrated by a rotary evaporator
  4. addition500 mL of water was added to the residue
  5. extractionan extraction
  6. concentrationthe organic layer was concentrated by a rotary evaporator
  7. customThe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=20/1, volume ratio)

Sources & evidence

ORD record
ord-819e9ed3c969478a95ee910389950770
Source dataset
uspto-grants-2014_12
Patent number
US08912287B2

Reaction notes

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