1,2-Dichloroethane → HCID 86729501, compound

HRID 712496Notes

Reaction equation

HRID 712496 reaction equation
[OH:1][CH:2]1[CH:7]([OH:8])[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.Cl[CH2:17][CH2:18]Cl>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].[OH-].[Na+]>[O:8]1[CH:7]2[CH:2]([CH2:3][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:6]2)[O:1][CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 111,2-DichloroethaneHCID 22929427tert-Butyl 3,4-dihydroxypiperidine-1-carboxylate

Product 1

HCID 86729501HCID 86729501, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of tert-butyl 3,4-dihydroxypiperidine-1-carboxylate (300 mg, 1.38 mmol, 1 eq), 1,2-dichloroethane (6 mL) and TBAB (90 mg, 0.28 mmol, 0.2 eq) in 35% NaOH (10 mL) aqueous solution was heated at 55° C. for 72 h, then cooled to room temperature and extracted with CH2Cl2 (100 mL). The organic phase was washed with water (30 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by a silica gel column chromatography (20:1 (v/v) CH2Cl2/MeOH) to afford the title compound as pale yellow oil (250 mg, 75.00%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 244.2 (M+1).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with CH2Cl2 (100 mL)
  3. washThe organic phase was washed with water (30 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by a silica gel column chromatography (20:1 (v/v) CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-1119e5cd6b714aa79f5924927beffac5
Source dataset
uspto-grants-2015_11
Patent number
US09181277B2

Reaction notes

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