1-Bromopropane → HCID 56622881, compound
Reaction equation
[CH3:1][N:2]([CH3:27])[N:3]=[C:4]1[C@H:9](CCC)[CH2:8][C@H:7]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:5]12[CH3:6])[C:21]1[CH:20]=[CH:19][C:18]([O:25][CH3:26])=[CH:17][C:16]=1[CH2:15][CH2:14]3.BrCCC>>[CH3:27][N:2]([CH3:1])[N:3]=[C:4]1[CH2:9][CH2:8][C@H:7]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:5]12[CH3:6])[C:21]1[CH:20]=[CH:19][C:18]([O:25][CH3:26])=[CH:17][C:16]=1[CH2:15][CH2:14]3Participants
Procedure
According to 1(b) 5.4 g of 3-methoxy-16α-propyl-1,3,5(10)-estratrien17-one N,N-dimethylhydrazone, m.p. 83°-85° C., is obtained from 5.0 g of 3-methoxy-1,3,5(10)-estratrien-17-one N,N-dimethylhydrazone with 1-bromopropane after crystallization from acetonitrile. By reaction with CuCl2.2H2O according to 1(c) 4.1 g of 3-methoxy-16α-propyl-1,3,5(10)-estratrien-17-one, m.p. 98°-100° C. (from acetonitrile), is obtained from 5.0 g of hydrazone, and 3.2 g of the 17-ketone yields with sodium borohydride according to 1(d) 2.1 g of 3-methoxy-16α-propyl-1,3,5(10)-estratrien-17β-ol, m.p. 54°-56° C. (from acetonitrile). By Birch reduction, acid hydrolysis, reaction with pyridine hydrobromide perbromide, acetylation in the 17-position, ketalization and deketalization in the 3-position 17β-acetoxy-16α-propyl-5(10)-9(11)-estradien-3-one is obtained as an oil.
Sources & evidence
- ORD record
- ord-e361ee79313f4fd38cde509b7495a005
- Source dataset
- uspto-grants-1982_06
- Patent number
- US04333928
Reaction notes
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