(9R)-9-acetyl-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione → 9(R)-bromoacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

HRID 464011Notes

Reaction equation

HRID 464011 reaction equation
[C:1]([C@:4]1([OH:26])[CH2:21][C:20]2[C:19]([OH:22])=[C:18]3[C:9]([C:10](=[O:24])[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=4[C:17]3=[O:23])=[C:8]([OH:25])[C:7]=2[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C1CNC(=O)C1.[Br:33][Br-]Br>O1CCCC1>[Br:33][CH2:2][C:1]([C@:4]1([OH:26])[CH2:21][C:20]2[C:19]([OH:22])=[C:18]3[C:9]([C:10](=[O:24])[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=4[C:17]3=[O:23])=[C:8]([OH:25])[C:7]=2[CH2:6][CH2:5]1)=[O:3]

Participants

3

Reactant 1

HCID 12823998(9R)-9-acetyl-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione

Product 1

HCID 131462679(R)-bromoacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 9(R)-acetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione ([α]D20 =-87° (c=0.1, CHCl3)) (11.5 g) with pyrrolidone hydrotribromide (18.19 g) was effected in tetrahydrofuran (1380 mg) at room temperature for 40 hours. After removing insoluble matters by filtration, the solvent was distilled off under reduced pressure to give 9(R)-bromoacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione, which was used in the next step without purification.

Workup

  1. customAfter removing insoluble matters
  2. filtrationby filtration
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-92674b865aa249dd944107dee59a239b
Source dataset
uspto-grants-1985_10
Patent number
US04545936

Reaction notes

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