2-Methylpentane → HCID 57791809, compound

HRID 1091756Notes

Reaction equation

HRID 1091756 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.Cl[CH2:16][C:17]([N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1)=[O:18].[OH-].[Na+].CCCC(C)C>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O.C(Cl)Cl.C1(C)C=CC=CC=1>[O:22]1[CH2:23][CH2:24][N:19]([C:17](=[O:18])[CH2:16][O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH2:20][CH2:21]1

Participants

9

Reactant 4

HCID 78922-MethylpentaneHCID 14798Sodium HydroxideHCID 74040Morpholine, 4-(chloroacetyl)-HCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 57791809HCID 57791809, compoundYield 94%

Reagents, catalysts & solvents 4

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

Tert-butyl 4-hydroxypiperidine-1-carboxylate (10 g, 49.69 mmol), tetrabutylammonium hydrogensulfate (0.844 g, 2.48 mmol) and 2-chloro-1-morpholinoethanone (8.13 g, 49.69 mmol) were added to toluene (75 mL) to this was added NaOH (40 g, 400.03 mmol) in water (45 mL) and the reaction was stirred at 25° C. overnight. The reaction mixture was quenched with water (100 mL), extracted with Et2O (3×75 mL), the organic layer was dried over MgSO4, filtered and evaporated to afford a white solid. This was redissolved in DCM and evaporated carefully to give a yellow gum, diethyl ether was added followed by iso-hexane until a cloudy solution was observed. The system was stirred to afford a solid which was collected by filtration and dried under vacuum to give the desired compound as a white solid (15.30 g, 94% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.45 (9H, s), 1.58-1.49 (OH, m), 1.72-1.61 (2H, m), 1.89-1.82 (2H, m), 3.12-3.06 (2H, m), 3.61-3.54 (6H, m), 3.68-3.67 (4H, m), 3.80-3.72 (1H, m), 4.18 (2H, s).

Workup

  1. customThe reaction mixture was quenched with water (100 mL)
  2. extractionextracted with Et2O (3×75 mL)
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customto afford a white solid
  7. customevaporated carefully
  8. customto give a yellow gum, diethyl ether
  9. additionwas added
  10. stirringThe system was stirred
  11. customto afford a solid which
  12. filtrationwas collected by filtration
  13. customdried under vacuum

Sources & evidence

ORD record
ord-147fce75ffaf45e98865fa53155e825c
Source dataset
uspto-grants-2012_03
Patent number
US08129380B2

Reaction notes

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