Water → HCID 12095711, compound

HRID 1986524Notes

Reaction equation

HRID 1986524 reaction equation
C[O:2][C:3]1(OC)[CH2:20][CH2:19][C:18]2[C@@:5](O)([CH2:6][CH2:7][C@@H:8]3[C:17]=2[C@@H:16]([C:21]2[CH:26]=[CH:25][C:24]([CH:27]4OCC(C)(C)C[O:28]4)=[CH:23][CH:22]=2)[CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:35])[CH2:4]1.[BH4-].[Na+].O>CO.C1COCC1>[OH:35][C@H:12]1[CH2:11][CH2:10][C@H:9]2[C@H:8]3[C:17]([C@@H:16]([C:21]4[CH:22]=[CH:23][C:24]([CH:27]=[O:28])=[CH:25][CH:26]=4)[CH2:15][C@:13]12[CH3:14])=[C:18]1[C:5](=[CH:4][C:3](=[O:2])[CH2:20][CH2:19]1)[CH2:6][CH2:7]3

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 68829489HCID 68829489, compound

Product 1

HCID 12095711HCID 12095711, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2.1 g of 3,3-dimethoxy-11β-[4-(5,5-dimethyl-1,3-dioxan-2-yl)phenyl]-5α-hydroxy-estr-9-en-17-one is dissolved in 25 ml of methanol/THF (1:1, V/V) and reduced at 23° C. with 303 mg of sodium borohydride. After 45 minutes, it is stirred into water, and the aqueous phase is extracted several times with methylene chloride. The organic phase is dried and evaporated under reduced pressure. The crude product [4-(3,3-dimethoxy-5α,17β-dihydroxy-estr-9-en-11β-yl)benzaldehyde-neopentylketal] is dissolved in 25 ml of acetone, and stirred with 2 ml of water and 283 mg of p-toluenesulfonic acid at room temperature for 8 hours. Then, it is poured into water and the precipitate is suctioned off. The purification of the crude product is carried out by chromatography with a toluene/acetone gradient on silica gel. 1.1 g of 4-(17β-hydroxy-3-oxoestra-4,9-dien-11β-yl)benzaldehyde is obtained.

Workup

  1. extractionthe aqueous phase is extracted several times with methylene chloride
  2. customThe organic phase is dried
  3. customevaporated under reduced pressure
  4. dissolutionThe crude product [4-(3,3-dimethoxy-5α,17β-dihydroxy-estr-9-en-11β-yl)benzaldehyde-neopentylketal] is dissolved in 25 ml of acetone
  5. additionThen, it is poured into water
  6. customThe purification of the crude product

Sources & evidence

ORD record
ord-bf3f0c50f7af4d12af383fbdfe16252c
Source dataset
uspto-grants-2009_06
Patent number
US07550451B2

Reaction notes

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