Acetic Acid → HCID 19995537, compound

HRID 1030663Notes

Reaction equation

HRID 1030663 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:18][CH:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:11][CH: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(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:18][CH:17]2[CH:12]([CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:11][C:10]1=[O:19])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724130Cornforth reagentHCID 19995517HCID 19995517, compound

Product 1

HCID 19995537HCID 19995537, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under argon to a solution of 3-tert-butoxycarbonylaminodecahydro-2-naphthalenol (0.27 g) in methylene chloride (5 ml) was added pyridinium dichromate (572 mg), molecular sieves 3A powder (791 mg) and acetic acid (100 μl). The reaction mixture was stirred for 50 minutes at room temperature. The black mixture was filtered through a silica gel column (60 g, elution with ethyl acetate:cyclohexane, 1:4) to give, after evaporation of solvents, the title compound as a viscous oil (165 mg).

Workup

  1. filtrationThe black mixture was filtered through a silica gel column (60 g, elution with ethyl acetate:cyclohexane, 1:4)
  2. customto give
  3. customafter evaporation of solvents

Sources & evidence

ORD record
ord-cf1fdc861f364553baed84df10db6b25
Source dataset
uspto-grants-1992_04
Patent number
US05106861

Reaction notes

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