7-Deoxytaxol → HCID 10929863, compound

HRID 279231Notes

Reaction equation

HRID 279231 reaction equation
[CH3:1][C:2]1[C@@H:19]([O:20]C([C@H](O)[C@@H](NC(C2C=CC=CC=2)=O)C2C=CC=CC=2)=O)[CH2:18][C@:14]2([OH:41])[C:15]([CH3:17])([CH3:16])[C:3]=1[C@@H:4]([O:58][C:59]([CH3:61])=[O:60])[C:5]([C@@:7]1([CH3:57])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][CH2:8]1)=[O:6]>C(Cl)Cl.CO>[CH3:1][C:2]1[C@@H:19]([OH:20])[CH2:18][C@:14]2([OH:41])[C:15]([CH3:16])([CH3:17])[C:3]=1[C@@H:4]([O:58][C:59]([CH3:61])=[O:60])[C:5]([C@@:7]1([CH3:57])[C@H:12]([C@@H:13]2[O:42][C:43]([C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=2)=[O:44])[C@:11]2([O:53][C:54]([CH3:56])=[O:55])[CH2:51][O:52][C@@H:10]2[CH2:9][CH2:8]1)=[O:6]

Participants

4

Reactant 1

HCID 99189837-Deoxytaxol

Product 1

HCID 10929863HCID 10929863, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

(2) To a solution of 7-deoxy paclitaxel (461 mg, 0.55 mmol) in 20 mL of methylene chloride and 0.4 mL of methanol was added Bu4NBH4 (283 mg, 1.1 mmol) and the solution stirred for 24 hours. The solution was quenched with saturated NH4Cl and extracted with ethyl acetate. The solution was dried over MgSO4 and concentrated. The residue was chromatographed over silica gel using hexane-ethyl acetate (1:1) to give 249 mg of product (79%).

Workup

  1. customThe solution was quenched with saturated NH4Cl
  2. extractionextracted with ethyl acetate
  3. dry with materialThe solution was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-f4318bb2d32346678dd0684effc55fdf
Source dataset
uspto-grants-2002_03
Patent number
US06362217B1

Reaction notes

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