Triacetoxyperiodinane → HCID 15078247, compound

HRID 2249104Notes

Reaction equation

HRID 2249104 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C@H:10]1[OH:19])=[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[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:11][C:10]1=[O:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 15078243HCID 15078243, compound

Product 1

HCID 15078247HCID 15078247, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon to (+)-trans-3-tert butoxycarbonylamino-1,2,3,4-tetrahydro-2-naphthalenol (70 mg) in methylene chloride (1 ml) was added Dess-Martin periodinane (172 mg). The mixture was stirred for 1 hour at room temperature under argon and filtered through a silica gel column [10 g, elution with ethyl acetate: cyclohexane mixtures. 1:9 (150 ml) and 2:8 (50 ml)]. Evaporation of solvent gave a solid which was recrystallized from pentane to yield the title compound as white needles, m.p. 76° C.

Workup

  1. filtrationfiltered through a silica gel column [10 g, elution with ethyl acetate: cyclohexane mixtures. 1:9 (150 ml) and 2:8 (50 ml)]
  2. customEvaporation of solvent
  3. customgave a solid which
  4. customwas recrystallized from pentane

Sources & evidence

ORD record
ord-fb5837a16d2349dab2abb451cb4c3959
Source dataset
uspto-grants-1991_08
Patent number
US05041673

Reaction notes

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