Acetic Acid → HCID 24901452, compound

HRID 2249102Notes

Reaction equation

HRID 2249102 reaction equation
C(OC([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)(C)(C)C.[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:52]>C1CCCCC1>[ClH:52].[NH2:8][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]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 2724130Cornforth reagentHCID 15078243HCID 15078243, compound

Product 1

HCID 24901452HCID 24901452, compound

Reagents, catalysts & solvents 1

HCID 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-e110e694c08941709cc6fef0ac7ac7c2
Source dataset
uspto-grants-1991_08
Patent number
US05041673

Reaction notes

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