Sodium Thiosulfate → tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylate

HRID 473809Notes

Reaction equation

HRID 473809 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[O:1]=[CH:2][CH2:3][CH:4]1[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 516892Sodium BicarbonateHCID 8541401-(tert-Butoxycarbonyl)-4-(2-hydroxyethyl)piperidine

Product 1

HCID 10353694tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-hydroxyethyl)piperidine-1-carboxylate (0.6 g, 2.6 mmol) in dichloromethane (30 mL) was added Dess-Martin-periodinane (1.2 g, 2.8 mmol), and the mixture was stirred at room temperature for 90 min. A 10% aqueous solution of sodium thiosulfate (15 mL) was added followed by saturated sodium bicarbonate (15 mL), and the biphasic mixture was stirred at room temperature for 1 h. The layers were separated, the aqueous layer was extracted twice with dichloromethane. The combined organic layers were washed with saturated sodium bicarbonate, and brine, dried over sodium sulfate, filtered and concentrated to afford tert-butyl 4-(oxoethyl)piperidine-1-carboxylate that was used directly without further purification.

Workup

  1. stirringthe biphasic mixture was stirred at room temperature for 1 h
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with dichloromethane
  4. washThe combined organic layers were washed with saturated sodium bicarbonate, and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d3b69adf36b6494db11cea5c9f2c5e97
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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