Triacetoxyperiodinane → HCID 19995529, compound

HRID 1030657Notes

Reaction equation

HRID 1030657 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)[C@@H:11]([O:19][CH:20]([CH3:22])[CH3:21])[C@@H:10]1[OH:23])=[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)[CH:11]([O:19][CH:20]([CH3:21])[CH3:22])[C:10]1=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 18646598HCID 18646598, compound

Product 1

HCID 19995529HCID 19995529, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon to a solution of (±)-(1R,2R,3R)-3-tert-butoxycarbonylamino -1,2,3,4-tetrahydro-1-isopropyloxy-2-naphthalenol (50 mg) in anhydrous methylene chloride (4 ml) was added Dess-Martin periodinane (100 mg). Agitation was maintained at room temperature for 2 hours. The reaction mixture was filtered on a silica gel column (10 g, elution ethyl acetate:cyclohexane, 1:9) to afford the title compound as an oil (38 mg).

Workup

  1. filtrationThe reaction mixture was filtered on a silica gel column (10 g, elution ethyl acetate:cyclohexane, 1:9)

Sources & evidence

ORD record
ord-6b28723efe0748dcb0c6b1b99bf73c92
Source dataset
uspto-grants-1992_04
Patent number
US05106861

Reaction notes

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