HCID 54775648, compound → HCID 117737813, compound

HRID 1518973Notes

Reaction equation

HRID 1518973 reaction equation
[CH2:1]([Li])CCC.[CH:6]1([C:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=O)[CH2:8][CH2:7]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH:6]1([C:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]2)=[CH2:1])[CH2:8][CH2:7]1

Participants

5

Reactant 2

HCID 54775648HCID 54775648, compoundHCID 178418339Butyllithium

Product 1

HCID 117737813HCID 117737813, compoundYield 83.5%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Dissolve methyltriphenylphosphonium bromide (20.26 g, 55.6 mmol) in THF (200 mL) and cool to −78° C. Add butyllithium (20.2 mL, 50.5 mmol) and stir at −78° C. for 15 minutes. Warm to ambient temperature and add a solution of tert-butyl 4-(cyclopropylcarbonyl)piperidine-1-carboxylate in THF (5 mL) dropwise. Stir the mixture overnight at ambient temperature. Quench with 50% saturated sodium bicarbonate solution, extract twice with diethyl ether and twice with EtOAc. Combine the organic extracts; wash with brine; dry over sodium sulphate; collect the filtrate; and concentrate under vacuum. Add a mixture of 1:1 diethyl ether:hexane (20 mL) and filter. Concentrate the filtrate under vacuum and purify via flash column chromatography to give the title compound (5.3 g, 83.5%). MS (m/z): 196 (M+1-tBu)

Workup

  1. temperatureWarm to ambient temperature
  2. customQuench with 50% saturated sodium bicarbonate solution
  3. extractionextract twice with diethyl ether and twice with EtOAc
  4. washwash with brine
  5. dry with materialdry over sodium sulphate
  6. customcollect the filtrate
  7. concentrationand concentrate under vacuum
  8. additionAdd
  9. additiona mixture of 1:1 diethyl ether
  10. filtrationhexane (20 mL) and filter
  11. concentrationConcentrate the filtrate under vacuum
  12. custompurify via flash column chromatography

Sources & evidence

ORD record
ord-80bf3c3614c545ea99a25d07866efeac
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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