Isopropanol → HCID 18646614, compound

HRID 2249128Notes

Reaction equation

HRID 2249128 reaction equation
[C:1]1([C:7]2[O:8][C@H:9]3[CH:19]([OH:20])[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[CH2:12][C@H:10]3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(O)(C)(C)C.C(O)(C)C>C(Cl)Cl>[C:1]1([C:7]2[O:8][C@H:9]3[C:19](=[O:20])[C:18]4[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=4[CH2:12][C@H:10]3[N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 6386tert-ButanolHCID 159087TriacetoxyperiodinaneHCID 18646613HCID 18646613, compound

Product 1

HCID 18646614HCID 18646614, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon to a solution of (±)-(3aR,9aR)-3a, 4,9,9a-tetrahydro 2-phenyl-naphth-[2,3-d]oxazol-9-ol in methylene chloride (10 ml) was added Dess Martin periodinane (640 mg) and tert-butylalcohol (56 mg). After 5 hours stirring at room temperature, isopropanol was added and the reaction mixture was filtered on a silica gel column (elution with cyclohexane: ethyl acetate, 40:1). Evaporation of solvents gave the title compound as an oil (150 mg).

Workup

  1. filtrationthe reaction mixture was filtered on a silica gel column (elution with cyclohexane: ethyl acetate, 40:1)
  2. customEvaporation of solvents

Sources & evidence

ORD record
ord-efa78df632774d05ab66a7964590de4a
Source dataset
uspto-grants-1991_08
Patent number
US05041673

Reaction notes

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