2-Chloro-N,N-diethyl-1,1,2-trifluoroethan-1-amine → 3beta-Hydroxy-7beta-ethenyl-5-androsten-17-one

HRID 861638

Reaction equation

HRID 861638 reaction equation
C([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]2=[O:28])[CH2:10]1)C1C=CC=CC=1.C(N([CH2:38][CH3:39])C(F)(F)C(Cl)F)C>>[OH:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:11](=[CH:12][C@H:13]([CH:38]=[CH2:39])[C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]2=[O:28])[CH2:10]1

Participants

3

Reactant 2

HCID 1361842-Chloro-N,N-diethyl-1,1,2-trifluoroethan-1-amineHCID 537649083beta-Benzyloxy-5-androsten-17-one

Product 1

HCID 676483413beta-Hydroxy-7beta-ethenyl-5-androsten-17-one

Procedure

Reaction of 3β,16α-dihydroxyandrost-5-en-17-one 3β-acetate 1 with a fluorinating agent such as diethyl (2-chloro-1,1,2-trifluoroethyl)amine affords 16α-fluoro-3β-hydroxyandrost-5-en-17-one 3-acetate 3. Hydrolysis of the ester with aqueous acid yields 16α-fluoro-3β-hydroxyandrost-5-en-17-one, 2a. ##STR47##

Sources & evidence

ORD record
ord-990edd6dac1548d3a5c5d4640812abd9
Source dataset
uspto-grants-1998_02
Patent number
US05714481

Linked notes

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