Acetic Acid → HCID 15078247, compound

HRID 1030634Notes

Reaction equation

HRID 1030634 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].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1.C(O)(=O)C.C(OCC)(=O)C>C(Cl)Cl.C1CCCCC1>[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

7

Reactant 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2724130Cornforth reagentHCID 15078243HCID 15078243, compound

Product 1

HCID 15078247HCID 15078247, compoundYield 31.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

Under argon to a solution of trans 3 tert-butoxycarbonylamino 1,2,3,4-tetrahydro-2-naphthalenol (2.02 g) in methylene chloride (40 ml) was added pyridinium dichromate (4.3 g), molecular sieves 3A (6.3 g) and acetic acid (0.76 ml). After 1 hour stirring at room temperature the mixture was poured on a silica gel column (120 g, elution with ethyl acetate: cyclohexane, 1:3) to afford a crude material which was recrystallized from a diethyl ether/cyclohexane mixture to give the title compound (634 mg) as a white solid, m.p. 104-105° C.

Workup

  1. customto afford a crude material which
  2. customwas recrystallized from a diethyl ether/cyclohexane mixture

Sources & evidence

ORD record
ord-72acc5dda9a8492bb426011658d6452d
Source dataset
uspto-grants-1992_04
Patent number
US05106861

Reaction notes

Loading…