Triacetoxyperiodinane → HCID 10867910, compound

HRID 2424256Notes

Reaction equation

HRID 2424256 reaction equation
[C:1]([NH:11][CH:12]([CH2:15][OH:16])[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[C:1]([NH:11][C@H:12]([CH:13]=[O:14])[CH2:15][OH:16])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 10585281N-CBZ-2-AMINO-1,3-PROPANEDIOL

Product 1

HCID 10867910HCID 10867910, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound (19) was prepared as described for compound (9). To a solution of 80 mmol of Cbz-O-Bn serinol (18) in 200 mL of dry dichloromethane, kept at room temperature under nitrogen, was added 88 mmol of Dess-Martin periodinane, and the reaction stirred for 2.5 hours, and then quenched by addition of 400 mL of 10% aqueous sodium thiosulfate solution. The layers were separated, and the organic layer concentrated, diluted with 300 mL of ethyl ether, and washed three times with a saturated aqueous bicarbonate solution containing 10% sodium thiosulfate, dried over magnesium sulfate, and concentrated. Compound (19) was obtained in 99% crude yield, and used without further purification. 1H NMR δ (CDCl3) 3.69-3.78 (dd, 1H, CH2O), 3.99-4.06 (dd, 1H, CH2O), 4.37-4.46 (m, 1H, CHN), 4.47-4.52 (d, 2H, CH2O), 5.14 (s, 2H, CH2O), 5.65-5.75 (br. d, 1H, NH), 7.14-7.48 (a series of m, 9H, Ph), 7.98-8.08 (dd, 1H, Ph), 9.63 (s, 1H, CHO).

Workup

  1. customCompound (19) was prepared
  2. customkept at room temperature under nitrogen
  3. customquenched by addition of 400 mL of 10% aqueous sodium thiosulfate solution
  4. customThe layers were separated
  5. concentrationthe organic layer concentrated
  6. additiondiluted with 300 mL of ethyl ether
  7. washwashed three times with a saturated aqueous bicarbonate solution
  8. additioncontaining 10% sodium thiosulfate
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-337a1ea76c7143f38b686328b52b828e
Source dataset
uspto-grants-2011_06
Patent number
US07964181B2

Reaction notes

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