Tetrahydrofuran → HCID 71459533, compound

HRID 990700Notes

Reaction equation

HRID 990700 reaction equation
[CH3:1][C:2]([CH3:46])=[CH:3][CH2:4][CH2:5][C@@:6]1([CH3:45])[O:15][C:14]2[C:13]([CH2:16][CH:17]=[C:18]([CH3:20])[CH3:19])=[C:12]3[O:21][C@@:22]45[C@@:32]6([CH2:37]/[CH:38]=[C:39](\[C:41]([OH:43])=[O:42])/[CH3:40])[O:33][C:34]([CH3:36])([CH3:35])[C@@H:23]4[CH2:24][C@H:25]([C:30]6=[O:31])[CH:26]=[C:27]5[C:28](=[O:29])[C:11]3=[C:10]([OH:44])[C:9]=2[CH:8]=[CH:7]1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].C1COCC1>C(Cl)Cl>[CH3:1][C:2]([CH3:46])=[CH:3][CH2:4][CH2:5][C@@:6]1([CH3:45])[O:15][C:14]2[C:13]([CH2:16][CH:17]=[C:18]([CH3:19])[CH3:20])=[C:12]3[O:21][C@@:22]45[C@@:32]6([CH2:37]/[CH:38]=[C:39](\[C:41]([OH:43])=[O:42])/[CH3:40])[O:33][C:34]([CH3:35])([CH3:36])[C@@H:23]4[CH2:24][C@H:25]([C:30]6=[O:31])[CH2:26][CH:27]5[C:28](=[O:29])[C:11]3=[C:10]([OH:44])[C:9]=2[CH:8]=[CH:7]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 3611392Lithium tri-s-butylborohydrideHCID 9852185Gambogic acid

Product 1

HCID 71459533HCID 71459533, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of gambogic acid (17 mg, 0.027 mmol) in methylenechloride (2 mL) was added L-selectride solution in THF (1.0 mL, 0.5 mmol) dropwise at −78° C. After 30 min of stirring, the reaction was quenched with 1 mL of 2 N HCl. The mixture was then allowed to warm to room temperature and was diluted with 1:1 hexane/EtOAc (50 mL). The resulting mixture was washed with water and brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (2:3 hexane/EtOAc/) to give the title compound as an oil (0.6 mg, 0.001 mmol, 4%). 1H NMR (CDCl3): 11.96 (s, 1H), 6.67 (d, J=10.2, 1H), 6.54 (t, J=6.6, 1H), 5.46 (d, J=10.2, 1H), 5.13-5.05 (m, 2H), 3.33-3.16 (m, 3H), 2.85 (d, J=13.8, 1H), 2.60 (d, J=8.7, 1H), 2.43 (s, 1H), 2.08 (m, 1H), 1.97 (s, 3H), 1.74 (s, 3H), 1.67 (s, 6H), 1.64 (s, 3H), 1.57 (s, 3H), 1.37 (s, 3H), 1.36 (d, J=6.9, 3H), 1.31-1.22 (m, 5H), 1.14 (s, 3H).

Workup

  1. customthe reaction was quenched with 1 mL of 2 N HCl
  2. additionwas diluted with 1:1 hexane/EtOAc (50 mL)
  3. washThe resulting mixture was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (2:3 hexane/EtOAc/)

Sources & evidence

ORD record
ord-824086d599f546adb5ff7a4a4a89672e
Source dataset
uspto-grants-2002_10
Patent number
US06462041B1

Reaction notes

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