Water → HCID 53446371, compound

HRID 2213038Notes

Reaction equation

HRID 2213038 reaction equation
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[N:11]1([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:16][CH2:15][CH:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13][CH2:12]1.Br[CH2:35][CH2:36][CH:37]=[CH2:38].O>O1CCCC1>[CH2:38]([C:14]1([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13][CH2:12][N:11]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:16][CH2:15]1)[CH2:37][CH:36]=[CH2:35]

Participants

6

Reactant 4

HCID 962WaterHCID 21241Homoallyl bromideHCID 2733832Lithium HexamethyldisilazideHCID 222559134-Benzyl 1-tert-butyl piperidine-1,4-dicarboxylate

Product 1

HCID 53446371HCID 53446371, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Lithium hexamethyldisilazide (1M in tetrahydrofuran, 15.7 mL, 15.7 mmol) was added dropwise to a stirred, cooled (−78° C.) solution of 1-(1,1-dimethylethyl) 4-phenylmethyl 1,4-piperidinedicarboxylate (2.50 g, 7.83 mmol) in tetrahydrofuran (50 mL) and the mixture was stirred at −78° C. for 2 hours. 4-Bromo-1-butene (1.99 mL, 19.6 mmol) was added dropwise and the mixture was stirred at −78° C. for 1 hour, then at room temperature for 2 hours. Water (100 mL) was added and the mixture was extracted with ethyl acetate (2×100 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (90:10) to give the title compound (1.07 g, 37%). 1H NMR (400 MHz CDCl3) δ 7.4–7.3 (5H, m), 5.75–5.6 (1H, m), 5.15 (2H, s), 4.93 (1H, br d, J 7 Hz), 4.90 (1H, br s), 3.95–3.75 (2H, m), 2.93–2.78 (2H, m), 2.13 (2H, br d, J 10 Hz), 1.95–1.85 (2H, m), 1.65–1.55 (2H, m), 1.44 (9H, s), and 1.43–1.30 (2H, m).

Workup

  1. stirringthe mixture was stirred at −78° C. for 1 hour
  2. waitat room temperature for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate (2×100 mL)
  4. dry with materialThe combined organic fractions were dried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluting with isohexane/EtOAc (90:10)

Sources & evidence

ORD record
ord-8cf16cbefa77473bae626586e5ed824c
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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