Water → HCID 131733083, compound

HRID 1518957Notes

Reaction equation

HRID 1518957 reaction equation
[H-].[Na+].[OH:3][C@H:4]1[C@H:9]([CH:10]([CH3:12])[CH3:11])[CH2:8][CH2:7][N:6]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:5]1.I[CH2:21][CH3:22].O>CN(C=O)C>[CH2:21]([O:3][C@H:4]1[C@H:9]([CH:10]([CH3:11])[CH3:12])[CH2:8][CH2:7][N:6]([C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14])[CH2:5]1)[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 6340Iodoethane2×HCID 24758Sodium hydrideHCID 131733082HCID 131733082, compound

Product 1

HCID 131733083HCID 131733083, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (69 mg, 1.73 mmol) to a solution of trans-tert-butyl 3-hydroxy-4-isopropyl-piperidine-1-carboxylate (300 mg, 1.23 mmol) in anhydrous DMF (2.5 mL) at ambient temperature. Stir the mixture for 25 minutes and then add iodoethane (112 μL, 1.48 mmol). Stir the mixture overnight. Add additional iodoethane (59.3 μL, 0.74 μmol) and stir the mixture for 3 h, then add water. Extract the aqueous layer with EtOAc, combine the organic layers. Sequentially wash the combined organic layers with water then brine; dry over anhydrous sodium sulphate; filter; collect the filtrate; and then remove the solvent under vacuum. Purify the compound by silica gel chromatography eluting with hexane:ethyl acetate (0%, 2%, 4% and 6% ethyl acetate) to obtain the title compound as a waxy solid (260 mg, 78%). MS (m/z): 216 (M-tBu+1)

Workup

  1. stirringStir the mixture overnight
  2. stirringstir the mixture for 3 h
  3. extractionExtract the aqueous layer with EtOAc
  4. washSequentially wash the combined organic layers with water
  5. dry with materialdry over anhydrous sodium sulphate
  6. filtrationfilter
  7. customcollect the filtrate
  8. customand then remove the solvent under vacuum
  9. customPurify the compound by silica gel chromatography
  10. washeluting with hexane

Sources & evidence

ORD record
ord-a7d15726563449b99fd376fd33faac3b
Source dataset
uspto-grants-2015_07
Patent number
US09073856B2

Reaction notes

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