Propanoic acid, 2-bromo-2-methyl-, ethyl ester → HCID 59652035, compound

HRID 2042587Notes

Reaction equation

HRID 2042587 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:34]([O:36][C:37](=[O:42])[C:38](Br)([CH3:40])[CH3:39])[CH3:35]>C1COCC1.C1(C)C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH2:22][C:38]([C:37]([O:36][CH2:34][CH3:35])=[O:42])([CH3:40])[CH3:39])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 3251421Potassium bis(trimethylsilyl)amideHCID 59652023HCID 59652023, compound

Product 1

HCID 59652035HCID 59652035, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 4-(5-acetyl-pyridin-2-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (1.36 g, 4.24 mmol) in THF (15 mL) at −78° C. was added 0.5M potassium bis(trimethylsilyl)amide in toluene (17 mL) and stirred for 30 min before adding 2-bromo-2-methyl-propionic acid ethyl ester (1.25 mL, 8.49 mmol) at −78° C. After overnight stirring at r.t., the reaction was quenched with 1N HCl, extracted with dichloromethane, washed with water/brine, dried over sodium sulfate, and concentrated. The product was purified using a Single Step column (7:3 hexanes:ethyl acetate) to obtain 0.458 g (25%); MS m/z 435 (M+H).

Workup

  1. stirringAfter overnight stirring at r.t.
  2. customthe reaction was quenched with 1N HCl
  3. extractionextracted with dichloromethane
  4. washwashed with water/brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified
  8. customto obtain 0.458 g (25%)

Sources & evidence

ORD record
ord-edffbf0999fa46c897d3bbd434280525
Source dataset
uspto-grants-2013_11
Patent number
US08586588B2

Reaction notes

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