Sodium Sulfate → HCID 53312285, compound

HRID 1401811Notes

Reaction equation

HRID 1401811 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([OH:33])[CH2:15][NH:16][C:17]([C:19]2[CH:28]=[CH:27][C:26]3[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]([CH3:32])([CH3:31])[C:21]=3[CH:20]=2)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:33])[CH2:15][NH:16][C:17]([C:19]2[CH:28]=[CH:27][C:26]3[C:25]([CH3:30])([CH3:29])[CH2:24][CH2:23][C:22]([CH3:32])([CH3:31])[C:21]=3[CH:20]=2)=[O:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 53312290HCID 53312290, compound

Product 1

HCID 53312285HCID 53312285, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.15 g (2.51 mmol) of 4-{1-hydroxy-2-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carbonyl)amino]ethyl}piperidine-1-carboxylic acid tert-butyl ester from step a was dissolved in 20 ml of DCM, and 15.61 ml (7.52 mmol) of Dess-Martin periodinane were added. The reaction mixture was stirred at room temperature for 30 min, 20 ml of a saturated sodium hydrogencarbonate solution and 5 ml of a saturated sodium sulfate solution were added, and the mixture was stirred vigorously for 30 min. The organic phase was separated off, and the water phase was extracted again with DCM. The organic phases were combined, dried, stripped off to dryness and purified by means of flash chromatography on silica gel.

Workup

  1. stirringthe mixture was stirred vigorously for 30 min
  2. customThe organic phase was separated off
  3. extractionthe water phase was extracted again with DCM
  4. customdried
  5. custompurified by means of flash chromatography on silica gel

Sources & evidence

ORD record
ord-0f951dfe744543bf82e6a36781bd0857
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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