Hydrogen Peroxide → 17beta-Tetrahydropyranyloxy-4beta-hydroxy-5alpha-androstane

HRID 27332Notes

Reaction equation

B.[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C:18](=[CH:19][CH2:20][CH2:21][CH2:22]1)[CH2:17][CH2:16]3.[OH-:28].[Na+].OO>O1CCCC1.O>[O:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C@H:18]([C@@H:19]([OH:28])[CH2:20][CH2:21][CH2:22]1)[CH2:17][CH2:16]3

Participants

Conditions

Temperature: 0 °C

Procedure

To a cooled solution (0° C.) of 5 ml. of 1 M borane in tetrahydrofuran in 2.7 ml. of dry tetrahydrofuran was added 500 mg. (1.4 millimole) of the product of Step C. in 2.0 ml. of dry tetrahydrofuran. The clear solution was stirred for 1 hr. at room temperature and then cooled to 0° C. and treated with 5 ml. of 2.5 N sodium hydroxide followed by 4 ml. of 30% hydrogen peroxide. The solution was stirred for 1 hr. at room temperature, diluted with water and extracted with ethyl ether, washed with water, brine, dried and evaporated to an oily crystalline material. The product was washed with cold methanol and pumped dry to give 175 mg. of final product having a m.p. of 167°-170° C.

Workup

customTo a cooled solution (0° C.) of 5 ml
additiontreated with 5 ml
stirringThe solution was stirred for 1 hr
extractionextracted with ethyl ether
washwashed with water, brine
customdried
customevaporated to an oily crystalline material
washThe product was washed with cold methanol
custompumped dry
customto give 175 mg

Sources & evidence

ORD record: ord-f7b4b13f31f1474b91baa4a400875309
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04220775

Reaction notes

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