tert-Butanol → HCID 19868636, compound

HRID 330490Notes

Reaction equation

HRID 330490 reaction equation
[OH:1][C:2]1[CH:17]=[C:16]([OH:18])[C:5]2[C:6](O)=[C:7]3[N:12]([C:13](=[O:14])[C:4]=2[CH:3]=1)[CH2:11][CH2:10][CH2:9][CH2:8]3.C(O)(C)(C)C>C(O)(=O)C>[OH:1][C:2]1[CH:17]=[C:16]([OH:18])[C:5]2[CH:6]=[C:7]3[N:12]([C:13](=[O:14])[C:4]=2[CH:3]=1)[CH2:11][CH2:10][CH2:9][CH2:8]3

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 19868617HCID 19868617, compound

Product 1

HCID 19868636HCID 19868636, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Shake a 25° C. mixture of 1,2,3,4-tetrahydro-8,10,11-trihydroxy-6H-benzo[b]quinolizin-6-one (2.00 g), rodium-on-aluminum oxide (1.10 g), and tert.-butanol (220 ml) containing acetic acid (1 ml) under a hydrogen pressure of 60 psi. For continuous shaking of the pressurized mixture, use a Paar apparatus; and for complete reaction, shake the mixture for at least 72 hrs. Then open the vessel and filter the mixture, washing the collected catalyst with tert.-butanol. Combine and concentrate the filtrates, and partition the residue between ethyl acetate and IM sodium bicarbonate solution. Sequentially wash the separated organic layer with 0.1N hydrochloric acid solution, with water, and with brine. Filter the dried solution and concentrate it to obtain 1,2,3,4-tetrahydro-8,10-dihydroxy-6H-benzo[b]quinolizin-6-one, m.p.214°-215° C. (from EtOAc).

Workup

  1. customand for complete reaction, shake the mixture for at least 72 hrs
  2. filtrationThen open the vessel and filter the mixture
  3. washwashing the collected catalyst with tert.-butanol
  4. concentrationCombine and concentrate the filtrates
  5. custompartition the residue between ethyl acetate and IM sodium bicarbonate solution
  6. washSequentially wash the separated organic layer with 0.1N hydrochloric acid solution
  7. filtrationFilter the dried solution
  8. concentrationconcentrate it

Sources & evidence

ORD record
ord-885a97f43d1345879238e2e3f0616096
Source dataset
uspto-grants-1990_01
Patent number
US04897391

Reaction notes

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