Sodium Chloride → HCID 69916328, compound

HRID 1837264Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

5.0 g of 7α-(5-chloropentyl)-11β-fluoro-3-hydroxy-estra-1,3,5(10)-trien-17-one is dissolved in 100 ml of methanol and mixed in portions at 0° C. with 0.96 g of sodium borohydride. After 30 minutes of stirring at 0° C., the reaction mixture is added to semi-saturated sodium chloride solution, extracted 3 times with ethyl acetate and washed once with saturated common salt solution. After drying on magnesium sulfate, it is concentrated by evaporation in a vacuum. Preparative column chromatography on silica gel with a hexane-ethyl acetate gradient yields 4.29 g of 7α-(5-chloropentyl)-11β-fluor-estra-1,3,5(10)-triene-3,17β-diol.

Workup

extractionextracted 3 times with ethyl acetate
washwashed once with saturated common salt solution
customAfter drying on magnesium sulfate, it
concentrationis concentrated by evaporation in a vacuum

Sources & evidence

ORD record: ord-9cf96fb16ddc4696ab2ac9f322d413d2
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06780855B2

Reaction notes

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