Sodium Hydroxide → HCID 15007453, compound

HRID 1461457Notes

Reaction equation

HRID 1461457 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C:11](=O)[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1.[F:21][C:22]([F:32])([F:31])[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26][NH2:27].C([BH3-])#N.[Na+].[OH-].[Na+]>CO.O1CCCC1.O.C(O)(=O)C>[Cl:1][C:2]1[CH:19]=[CH:18][C:17]2[C@@H:16]3[C@H:7]([C@H:8]4[C@@:12]([CH2:14][CH2:15]3)([CH3:13])[C@@H:11]([NH:27][CH2:26][C:25]3[CH:28]=[CH:29][CH:30]=[C:23]([C:22]([F:21])([F:31])[F:32])[CH:24]=3)[CH2:10][CH2:9]4)[CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 759623-(Trifluoromethyl)benzylamineHCID 5003444Sodium cyanoborohydride2×HCID 15007452HCID 15007452, compound

Product 1

HCID 15007453HCID 15007453, compoundYield 67.1%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound, 3-chloroestra-1,3,5(10)-trien-17-one (2.17 g) is added to a solution of 3-(trifluoromethyl)benzylamine (2.6 g) in methanol (200 ml) and tetrahydrofuran (200 ml) made acidic with acetic acid (1.5 ml). When the starting material is dissolved, sodium cyanoborohydride (0.72 g) is added, the mixture is stirred 24 hours, additional sodium cyanoborohydride (0.7 g) is and the mixture is stirred for another 21 hours. The mixture is diluted with water (200 ml), made basic with 50% sodium hydroxide and extracted with methylene chloride (3×100 ml). The combined extracts are washed with brine, dried over magnesium sulfate and the solvent is removed. The product is chromatographed on silica gel and recrystallized in methylene chloride/hexane to give the title compound (2.26 g).

Workup

  1. dissolutionWhen the starting material is dissolved
  2. stirringthe mixture is stirred for another 21 hours
  3. extractionextracted with methylene chloride (3×100 ml)
  4. washThe combined extracts are washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent is removed
  7. customThe product is chromatographed on silica gel
  8. customrecrystallized in methylene chloride/hexane

Sources & evidence

ORD record
ord-468c00c16c514beda65c2acbf6bbd672
Source dataset
uspto-grants-1991_12
Patent number
US05075434

Reaction notes

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