Triacetoxyperiodinane → HCID 59651970, compound

HRID 221826Notes

Reaction equation

HRID 221826 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][OH:23])=[CH:17][CH:16]=2)[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(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH:22]=[O:23])=[CH:19][CH:20]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59651909HCID 59651909, compound

Product 1

HCID 59651970HCID 59651970, compoundYield 35.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-[4-(2-hydroxyethyl)-phenoxy]piperidine-1-carboxylic acid tert-butyl ester (8.10 g, 25.2 mmol) in 90 mL of CH2Cl2 was cooled to 0° C. as Dess-Martin periodinane (11.2 g, 26.5 mmol) was added in portions. After stirred at rt overnight, the reaction was diluted with 100 mL of CH2Cl2, and washed with saturated NaHCO3 (5×100 mL), water, and dried over Na2SO4. Flash chromatography with 60% Et2O in hexane gave 2.83 g (35%) of 4-[4-(2-oxo-ethyl)-phenoxy]-piperidine-1-carboxylic acid tert-butyl ester: MS m/z 220 (M−Boc+H).

Workup

  1. additionwas added in portions
  2. washwashed with saturated NaHCO3 (5×100 mL), water
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-ee19c9e9590441c9818c3ac2d84268f5
Source dataset
uspto-grants-2012_06
Patent number
US08207168B2

Reaction notes

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