Triacetoxyperiodinane → HCID 67373398, compound

HRID 401936Notes

Reaction equation

HRID 401936 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH:10]([CH2:15][O:16][CH2:17][O:18][CH3:19])[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(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH:10]([CH2:15][O:16][CH2:17][O:18][CH3:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67372907HCID 67372907, compound

Product 1

HCID 67373398HCID 67373398, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-3-methoxymethoxymethyl-piperidine-1-carboxylic acid tert-butyl ester (Example 38, 9.1 mmol, 2.5 g) in 50 mL of DCM was added Dess-Martin reagent (10.8 mmol, 4.6 g). The mixture was stirred at room temperature for 2 h, then washed with saturated sodium bicarbonate solution, brine, dried, evaporated, the resulting residue was chromatographed with 9:1 hexane/EtOAc afforded 3-methoxymethoxymethyl-4-oxo-piperidine-1-carboxylic acid tert-butyl ester (2.2 g).

Workup

  1. washwashed with saturated sodium bicarbonate solution, brine
  2. customdried
  3. customevaporated
  4. customthe resulting residue was chromatographed with 9:1 hexane/EtOAc

Sources & evidence

ORD record
ord-aae3ad9bc00d42dda22be5d7a966a0b5
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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