Triacetoxyperiodinane → HCID 117697986, compound

HRID 1778530Notes

Reaction equation

HRID 1778530 reaction equation
[OH:1][CH:2]1[CH2:8][CH:7]2[N:9]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH:3]1[CH2:4][CH:5]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:6]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:24][O:23][C:21](=[O:22])[CH2:20][CH:5]1[CH2:4][CH:3]2[N:9]([C:10]([O:12][CH2:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:11])[CH:7]([CH2:8][C:2]2=[O:1])[CH2:6]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 117697489HCID 117697489, compound

Product 1

HCID 117697986HCID 117697986, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 109f (30 g, 0.09 mol, 1.0 eq) in DCM (800 mL) was added DMP (Dess-Martin Periodinane, 76.5 g, 0.18 mol, 2.0 eq) slowly at 0° C. The resulting mixture was stirred at room temperature for 16 h, and quenched with water. The solid was filtered off, the filtrate was washed with brine (500 mL), dried over Na2SO4 and concentrated. The residue was purified by silica gel (EA/PE=1:3) to give benzyl 3-(2-methoxy-2-oxo-ethyl)-6-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate 109g as a colorless oil (26.5 g, yield 88%). 1H NMR (400 MHz, DMSO-d6) δ: 7.46-7.30 (m, 5H), 5.15 (s, 2H), 4.61 (br, 1H), 4.00 (br, 1H), 3.58 (s, 3H), 2.77 (dd, J=7.2, 18.2 Hz, 1H), 2.41-2.30 (m, 3H), 2.28-2.10 (m, 3H), 1.49 (d, J=13.2 Hz, 1H), 1.38 (d, J=11.8 Hz, 1H); MS: calc'd (MH+) 332, measured (MH+) 332.

Workup

  1. customquenched with water
  2. filtrationThe solid was filtered off
  3. washthe filtrate was washed with brine (500 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel (EA/PE=1:3)

Sources & evidence

ORD record
ord-2018987f12ac442eada47a42efeafacc
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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