Triacetoxyperiodinane → HCID 117698042, compound

HRID 1778541Notes

Reaction equation

HRID 1778541 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH:6]1[CH2:13][CH:12]2[N:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:8]([CH2:9][O:10][CH2:11]2)[CH:7]1[OH:22])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[CH2:1]([O:3][C:4](=[O:23])[CH2:5][CH:6]1[CH2:13][CH:12]2[N:14]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH:8]([CH2:9][O:10][CH2:11]2)[C:7]1=[O:22])[CH3:2]

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 117697824HCID 117697824, compound

Product 1

HCID 117698042HCID 117698042, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 123d (960 mg, 3.0 mmol) in dichloromethane (30 mL) was added Dess-Martin reagent (2.54 g, 6.0 mmol) at 40° C. The reaction mixture was stirred for three hours, then another batch of Dess-Martin reagent (1.27 g, 3.0 mmol) was added. The reaction mixture was stirred overnight. The reaction mixture was poured into ice-water, and filtrated. The filtrate was washed with sodium bicarbonate solution and sodium sulphite solution, extracted with dichloromethane (50 mL) three times. The organic phase was dried over Na2SO4, and concentrated. The residue was purified by silica gel column to give tert-butyl 7-(2-ethoxy-2-oxo-ethyl)-6-oxo-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate 125b (780 mg, yield: 80%).

Workup

  1. stirringThe reaction mixture was stirred overnight
  2. filtrationfiltrated
  3. washThe filtrate was washed with sodium bicarbonate solution and sodium sulphite solution
  4. extractionextracted with dichloromethane (50 mL) three times
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-fbb98115974740d889903f099b93982c
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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