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Pentane → HCID 23114648, compound

HRID 2080373
Notes
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Reaction equation

HRID 2080373 reaction equation
C([Li])(C)(C)C.CCCCC.[Si:11]([O:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C:23]1=[O:28])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].[Br-:29].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC>CCCCCC.O.O1CCCC1>[Br:29][CH:24]1[CH2:25][CH2:26][CH2:27][N:22]([CH2:21][CH2:20][CH2:19][O:18][Si:11]([C:14]([CH3:16])([CH3:17])[CH3:15])([CH3:13])[CH3:12])[C:23]1=[O:28]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 8003PentaneHCID 231147471-(3-{[tert-Butyl(dimethyl)silyl]oxy}propyl)piperidin-2-oneHCID 23500184Tetra-n-butylammonium tribromideHCID 178418306HCID 178418306, compound

Product 1

HCID 23114648HCID 23114648, compoundYield 10.4%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent2×
HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

Under an argon atmosphere, t-butyl lithium (a 1.50M pentane solution, 1.40 ml, 2.10 mmol) was added dropwise to a tetrahydrofuran solution (5 ml) of 1-[3-(t-butyldimethylsilyloxy)propyl]piperidin-2-one (542 mg, 2.00 mmol) at −78° C. The reaction mixture was stirred at −78° C. for 15 minutes. After a tetrahydrofuran solution (5 ml) of tetrabutylammonium tribromide (1.16 g, 2.40 mmol) was added to the reaction mixture, the temperature of the resulting mixture was gradually raised to −40° C. under stirring. Water was added to the reaction mixture at −40° C. and then, the temperature of the mixture was raised to room temperature. The reaction mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and concentrated. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=2:3 eluate was concentrated to give the title compound (72.8 mg, 0.208 mmol, 10%) as a colorless oil.

Workup

  1. temperaturethe temperature of the resulting mixture was gradually raised to −40° C.
  2. stirringunder stirring
  3. temperaturethe temperature of the mixture was raised to room temperature
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washThe extract was washed with water and brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe residue thus obtained
  9. concentrationethyl acetate=2:3 eluate was concentrated

Sources & evidence

ORD record
ord-85234d62d942484c9123e0fcb34ddba2
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07932271B2

Reaction notes

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