Acetic Acid → HCID 69965370, compound

HRID 650355Notes

Reaction equation

HRID 650355 reaction equation
[BH4-].[Na+].C([O:6][C:7]1[C@:8]2([CH2:24][CH2:23][C@H:22]3[C@@H:13]([C@H:14]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38][C:39](=[O:41])[CH3:40])[CH2:15][C:16]4[CH:17]=[C:18]([O:25][CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH:19]=[CH:20][C:21]=43)[C:10]2=[CH:11][CH:12]=1)[CH3:9])(=O)C.C(O)(=O)C>C(O)C.O.O1CCCC1>[C:39]([O:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][C@@H:14]1[CH2:15][C:16]2[CH:17]=[C:18]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:19]=[CH:20][C:21]=2[C@@H:22]2[C@@H:13]1[C:10]1[C@@:8]([CH2:24][CH2:23]2)([CH3:9])[C@@H:7]([OH:6])[CH2:12][CH:11]=1)(=[O:41])[CH3:40]

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 57284264HCID 57284264, compound

Product 1

HCID 69965370HCID 69965370, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.25 g of sodium borohydride in 90 ml of ethanol and 18 ml of water is added in drops to a solution of 4.58 g of 17-acetoxy-7α-(5-acetoxypentyl)-3-benzyloxy-estra-1,3,5(10),14,16-pentaene in 26.8 ml of tetrahydrofuran and 161 ml of ethanol at room temperature, and the mixture is stirred for 1 hour. The reaction mixture is mixed with 4 ml of glacial acetic acid, concentrated by evaporation, and the residue is taken up in ethyl acetate. The organic phase is washed with sodium bicarbonate, dried on sodium sulfate and concentrated by evaporation. The residue is chromatographed on silica gel with hexane/ethyl acetate. 2.16 g of 7α-(5-acetoxypentyl)-3-benzyloxy-estra-1,3,5(10),14-tetraen-17β-ol is obtained as foam.

Workup

  1. concentrationconcentrated by evaporation
  2. washThe organic phase is washed with sodium bicarbonate
  3. customdried on sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica gel with hexane/ethyl acetate

Sources & evidence

ORD record
ord-5bd01adab1bf4b85855df44760a2d6b2
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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