Dichloromethane → Estra-1,3,5(10)-trien-17-ol, 4-amino-, (17β)-

HRID 1589141Notes

Reaction equation

HRID 1589141 reaction equation
S(O[C:9]1[CH:26]=[CH:25][C:24]2[C@@H:23]3[C@H:14]([C@H:15]4[C@@:19]([CH2:21][CH2:22]3)([CH3:20])[CH:18]([OH:27])[CH2:17][CH2:16]4)[CH2:13][CH2:12][C:11]=2[C:10]=1[N+:28]([O-])=O)(C(F)(F)F)(=O)=O.C(N(CC)CC)C.ClCCl>CO.[Pd]>[NH2:28][C:10]1[C:11]2[CH2:12][CH2:13][C@@H:14]3[C@@H:23]([C:24]=2[CH:25]=[CH:26][CH:9]=1)[CH2:22][CH2:21][C@@:19]1([CH3:20])[C@H:15]3[CH2:16][CH2:17][C@@H:18]1[OH:27]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 86740647HCID 86740647, compound

Product 1

HCID 13371421Estra-1,3,5(10)-trien-17-ol, 4-amino-, (17β)-Yield 25%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-nitroestra-1,3,5(10)-trien-3,17-diol 3-O-triflate (2.13 g, 4.74 mmol) in 100 ml of methanol containing triethylamine (6.60 , 4.8 mmol) and 10% Pd/C (430 mg. 20% by weight) was hydrogenated in a Parr apparatus at 16 psi for 5 hr. TLC using 95% dichlormethane 1% methanol showed one major product and 3 minor constituents. The reaction mixture was filtered through Celite and the filtrate was evaporated to dryness. The residue was dissolved in excess dichloromethane and the solution was washed with water. The extract was dried over sodium sulfate and filtered. The filtrate was evaporated to dryness. The residue crystallized from methanol as a cluster of colorless needles of 4-aminoestra-1,3,5(10)-trien-17β-ol; wt. 320 mg. (25% yield), mp 189°-192° C. Mass Spectrum: m/z 271 (M+), 237 (M--H2O+NH2). 1H NMR 7.23-6.51 (m, 3, H1, H2, H3 aromatic) 3.71-3.45 (t, 1, 17H), 2.57-1.23 (m, 18), 0.876 (s, 3, C18CH3).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe filtrate was evaporated to dryness
  3. dissolutionThe residue was dissolved in excess dichloromethane
  4. washthe solution was washed with water
  5. dry with materialThe extract was dried over sodium sulfate
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. customThe residue crystallized from methanol as a cluster of colorless needles of 4-aminoestra-1,3,5(10)-trien-17β-ol

Sources & evidence

ORD record
ord-3a3ad6775afc46c986059cbc02802b6c
Source dataset
uspto-grants-1986_02
Patent number
US04568673

Reaction notes

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