Triacetoxyperiodinane → HCID 57945204, compound

HRID 1697887Notes

Reaction equation

HRID 1697887 reaction equation
[C:1]([O:5][C:6]([NH:8][C@:9]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][C@H:10]1[CH2:12][CH2:13][OH:14])=[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]([NH:8][C@:9]1([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:11][C@H:10]1[CH2:12][CH:13]=[O:14])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 10635973HCID 10635973, compound

Product 1

HCID 57945204HCID 57945204, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R,2S)-ethyl 1-(tert-butoxycarbonylamino)-2-(2-hydroxyethyl)cyclopropanecarboxylate (9.70 g, 35.5 mmol) in DCM (300 ml) at 0° C. was added Dess-Martin periodinane (18.06 g, 42.6 mmol). The formed slurry was stirred at room temperature overnight. The reaction mixture was filtered through celite. The resulting filtrated was concentrated and this process was repeated one more time. Residue was purified by a silica gel column, eluted with 8:1, 4:1, 3:1, then 2:1 heaxane-EtOAc to yield (1R,2S)-ethyl 1-(tert-butoxycarbonylamino)-2-(2-oxoethyl)cyclopropanecarboxylate (6.15 g, 22.67 mmol, 63.9% yield) as a colorless oil. 1H NMR (CDCl3) δ 1.24 (t, J=7 Hz, 3H), 1.40-1.45 (m, 11H), 1.65-1.69 (m, 1H), 2.75-2.80 (m, 2H), 4.09-4.19 (m, 2H), 5.17 (b, 1H), 9.76 (s, 1H).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. filtrationThe resulting filtrated
  3. concentrationwas concentrated
  4. customResidue was purified by a silica gel column
  5. washeluted with 8:1, 4:1, 3:1

Sources & evidence

ORD record
ord-802412027e86402c8313cd74643ad7d1
Source dataset
uspto-grants-2012_04
Patent number
US08163921B2

Reaction notes

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