Triacetoxyperiodinane → HCID 19995578, compound

HRID 2249111Notes

Reaction equation

HRID 2249111 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[C@H:22]([OH:23])[CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][C:11]=2[CH2:10]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]([NH:8][CH:9]1[C:22](=[O:23])[CH2:21][C:20]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][C:11]=2[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67865972HCID 67865972, compound

Product 1

HCID 19995578HCID 19995578, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon to a solution of trans 2-tertbutoxycarbonylamino-1,2,3,4-tetrahydro-3-phenanthrenol (140 mg) in anhydrous methylene chloride (5 ml) was added Dess-Martin periodinane (281 mg). Agitation was maintained for 1 hour at room temperature and the reaction mixture was filtered on silica gel (30 g, elution with ethyl acetate:cyclohexane, 1:9). Evaporation of solvents gave the crude title compound (136 mg) which was recrystallized from a pentane/ethyl acetate mixture. The title compound was obtained as white needles (89 mg).

Workup

  1. filtrationthe reaction mixture was filtered on silica gel (30 g, elution with ethyl acetate:cyclohexane, 1:9)
  2. customEvaporation of solvents
  3. customgave the crude title compound (136 mg) which
  4. customwas recrystallized from a pentane/ethyl acetate mixture

Sources & evidence

ORD record
ord-d3f76c14fb4b4a52b0793b24686ef5a1
Source dataset
uspto-grants-1991_08
Patent number
US05041673

Reaction notes

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