Chlorosuccinimide → 3beta-Chloro-17beta-methoxy-5alpha-androstane

HRID 848785Notes

Reaction equation

O[C@@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[O:21][CH3:22])[CH2:3]1.[Cl:23]N1C(=O)CCC1=O>>[Cl:23][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[O:21][CH3:22])[CH2:3]1

Participants

Reactant 2

HCID 31398Chlorosuccinimide

HCID 128368613alpha-Hydroxy-17beta-methoxy-5alpha-androstane

Product 1

HCID 705647413beta-Chloro-17beta-methoxy-5alpha-androstane

Procedure

Following the general procedure of Example 28 and making non-critical variations 3α-hydroxy-17β-methoxy-5α-androstane (Example 27, 0.47 g.) is reacted with N-chlorosuccinimide for 2 hours. The mixture is extracted with SSB, concentrated, and chromatographed on silica gel eluting with ethyl acetate-hexane (5:95) to obtain the title compound, upon recrystallization from methanol, NMR (CDCl3) 0.74, 0.84, 3.16, 3.33 and 3.75 δ; MS (m/e) 324, 309, 292, 277 and 251.

Workup

extractionThe mixture is extracted with SSB
concentrationconcentrated
customchromatographed on silica gel eluting with ethyl acetate-hexane (5:95)

Sources & evidence

ORD record: ord-2f8436b6de5d4a3e820d3c817a976d6b
Source dataset: uspto-grants-1981_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04297350

Reaction notes

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