Sodium borohydride → HCID 22820392, compound
Reaction equation
[BH4-].[Na+].[CH2:3]([C@@H:5]1[CH2:10][C@H:9]2[C@H:11]3[C@H:20]([CH2:21][CH2:22][C@:7]2([CH3:8])[C@H:6]1[OH:25])[C:19]1[CH:18]=[CH:17][C:16]([O:23]C)=[CH:15][C:14]=1[CH2:13][CH2:12]3)[CH3:4].C1C=C[NH+]=CC=1.Br[Br-]Br.C(OCC)(=O)C.C(OC(C)C)(C)C>CO>[CH2:3]([C@@H:5]1[CH2:10][C@H:9]2[C@H:11]3[C:20]([CH2:21][CH2:22][C@:7]2([CH3:8])[C@H:6]1[OH:25])=[C:19]1[C:14](=[CH:15][C:16](=[O:23])[CH2:17][CH2:18]1)[CH2:13][CH2:12]3)[CH3:4]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
According to 1(b), 20.2 g of 16α-ethyl-3-methoxy-1,3,5(10)-estratrien-17-one, N,N-dimethylhydrazone, m.p. 101°-103° C. (from acetonitrile) is obtained from 20.4 g of 3-methoxy-1,3,5(10)-estratrien-17-one N,N-dimethylhydrazone after metallization and alkylation with 9.2 ml of bromoethane. By reaction with CuCl2.2H2O according to 1(c), the 17-ketone is obtained from the hydroazone and then, by reduction of the 17-ketone with sodium borohydride according to 1(d), 16.0 g of 16α-ethyl-3-methoxy-1,3,5(10)-estratrien-17β-ol, m.p. 75°-76° C. (from methanol) is prepared. 10.0 g of 16α-ethyl-3-methoxy-1,3,5(10)-estratrien-17β-ol is subjected analogously to 1(e) in succession to Birch reduction, acid hydrolysis, and reaction with pyridine hydrobromide perbromide, thus obtaining 7.8 g of 16α-ethyl-17β-hydroxy-4,9(10)-estradien-3-one, m.p. 132°-135° C. (from ethyl acetate/diisopropyl ether). This product is converted analogously to 1(f) with acetic anhydride/pyridine into the 17-acetate, m.p. 124°-126° C. (from ether) and analogously to 1(g) by ketalization and subsequent ketal cleavage into the 17β-acetoxy-16α-ethyl-5(10),9(11)-estradien-3-one.
Sources & evidence
- ORD record
- ord-30f7cf566a8b49e9a5b287ffe882f008
- Source dataset
- uspto-grants-1982_06
- Patent number
- US04333928
Reaction notes
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