Triacetoxyperiodinane → HCID 86657808, compound

HRID 1971968Notes

Reaction equation

HRID 1971968 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH2:14][OH:15])[C@H:10]([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)C2C1=CC=CC=2)=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@@H:11]([CH:14]=[O:15])[C@H:10]([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 86657809HCID 86657809, compound

Product 1

HCID 86657808HCID 86657808, compoundYield 116.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (±)-trans-4-hydroxymethyl-3-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester (Example 36, 2.17 mmol, 0.75 g) in anhydrous DCM (5 mL) at room temperature was added 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one (4.35 mmol, 1.85 g). The reaction was stirred for 1 hour. The reaction mixture was pre-absorbed on 6.5 g SiO2 and purified on 40 g SiO2 cartridge using a 20-40% ethyl acetate/hexanes gradient to give (±)-trans-4-formyl-3-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester (0.69 g).

Workup

  1. customThe reaction mixture was pre-absorbed on 6.5 g SiO2
  2. custompurified on 40 g SiO2 cartridge

Sources & evidence

ORD record
ord-ac52f903f2f94374820106b729ce1e03
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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