Sodium borohydride → 17beta-Hydroxy-7alpha-methyl-11-methyleneestr-4-en-3-one
Reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:18]2[C@@H:17]3[C@H:8]([C@H:9]4[C@@:13]([CH2:15][C:16]3=[CH2:21])([CH3:14])[C:12](=[O:22])[CH2:11][CH2:10]4)[C@H:7]([CH3:23])[CH2:6][C:5]=2[CH:4]=1.[BH4-].[Na+]>>[OH:22][C@H:12]1[CH2:11][CH2:10][C@H:9]2[C@H:8]3[C@H:17]([C:16](=[CH2:21])[CH2:15][C@:13]12[CH3:14])[C@@H:18]1[C:5](=[CH:4][C:3](=[O:2])[CH2:20][CH2:19]1)[CH2:6][C@H:7]3[CH3:23]Participants
3
Procedure
3-Methoxy-7α-methyl-11-methyleneestr-1,3,5(10)-trien-17-one (A-11) was subjected to sodium borohydride reduction of the 17-ketone function, Birch reduction with lithium/NH3(1), and acid hydrolysis and rearrangement to the title compound. Experimental details are as follows:
Sources & evidence
- ORD record
- ord-0ff013b2a6244c9f809840fab6999109
- Source dataset
- uspto-grants-2003_12
- Patent number
- US06670352B2
Reaction notes
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