Tetrabutylammonium Fluoride → HCID 69918189, compound

HRID 1838917Notes

Reaction equation

HRID 1838917 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][C:7](OC3CCCCO3)=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH2:29][CH:30]([O:35][SiH](C)C)C(C)(C)C)[CH3:27].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH2:28][CH2:29][CH2:30][OH:35])[CH3:27]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 137329509HCID 137329509, compound

Product 1

HCID 69918189HCID 69918189, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.3 g of 11β-fluoro-7α-{5-[(3-tert-butyldimethylsilyl-oxypropyl)methylamino]pentyl}-3-(tetrahydropyran-2-yloxy)oestra-1,3,5(10)-trien-17-one in 23 ml of tetra-hydrofuran are reacted at room temperature with 6 ml of tetrabutylammonium fluoride solution (1M in tetra-hydrofuran). After 2 hours, the mixture is diluted with ethyl acetate, washed with saturated sodium chloride solution, dried and concentrated in vacuo. Chromatography of the crude product on silica gel using a methylene chloride-methanol gradient affords 1.5 g of 11β-fluoro-7α-{5-[(3-hydroxypropyl)methylamino]-pentyl}oestra-1,3,5(10)-trien-17-one as a foam.

Workup

  1. washwashed with saturated sodium chloride solution
  2. customdried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cc0404fa8fbf45bb99f9ef390575dfcb
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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