Sophorophenolone → Lupinalbin A

HRID 1357060Notes

Reaction equation

HRID 1357060 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:7](=[O:22])[C:8]4[C:18]([OH:19])=[CH:17][C:16]([O:20]C)=[CH:15][C:9]=4[O:10][C:11]=3[O:12][C:13]=2[CH:14]=1.N1C(=O)CC[C@H]1C(O)=O.Cl>>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[C:7](=[O:22])[C:8]4[C:18]([OH:19])=[CH:17][C:16]([OH:20])=[CH:15][C:9]=4[O:10][C:11]=3[O:12][C:13]=2[CH:14]=1

Participants

3

Reactant 2

HCID 12083341SophorophenoloneHCID 67725173Pyr-HCl

Product 1

HCID 5324349Lupinalbin AYield 43.2%

Conditions

Temperature
190 °C

Procedure

A mixture consisting of 10 (0.17 g) and 7g Pyr-HCl was heated to 190° C. for 45 min. The reaction was allowed to cool and then partitioned between water and EtOAc. The EtOAc was dried over MgSO4, filtered, concentrated and chromatographed on silica gel (EtOAc/hexanes; 3:7) to give the product as a white solid (0.07 g): Mp 318-322 (dec); 1H NMR (DMSO-d6) δ 12.90 (s, 1H), 10.97 (br s, 1H), 9.99 (br s, 1H), 7.72 (d, 1H, J=8.4 Hz), 7.11 (d, 1H, J=2.1 Hz), 6.93 (dd, 1H, J=8.4 Hz, 2.1 Hz), 6.56 (d, 1H, J=2.1 Hz), 6.30 (d, 1H, J=2.1 Hz); MS FI (neg) 283 (M−H)−.

Workup

  1. temperatureto cool
  2. custompartitioned between water and EtOAc
  3. dry with materialThe EtOAc was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on silica gel (EtOAc/hexanes; 3:7)

Sources & evidence

ORD record
ord-c5739777e7904f29895b637c7b6c7cb4
Source dataset
uspto-grants-2003_07
Patent number
US06589980B2

Reaction notes

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