Hydrogen Peroxide → HCID 70614544, compound
Reaction equation
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].C(O)(=O)C.[OH:19][CH2:20][C@@:21]12[C@@H:38]3[C@H:29]([C@H:30]4[C@@:34]([CH2:36][CH2:37]3)([CH3:35])[C:33](=[O:39])[CH2:32][CH2:31]4)[CH2:28][CH2:27][C@H:26]1[CH2:25][C:24](=[O:40])[CH2:23][CH2:22]2.[OH-].[Na+].OO.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:35][C@:34]12[CH2:36][CH2:37][C@H:38]3[C@@H:29]([CH2:28][CH2:27][C@@H:26]4[C@:21]3([CH2:20][OH:19])[CH2:22][CH2:23][C@@H:24]([OH:40])[CH2:25]4)[C@@H:30]1[CH2:31][CH2:32][C@@H:33]2[OH:39]Participants
Conditions
- Temperature
- 0 °C
Procedure
A 1 M solution of lithium tri-sec-butylborohydride in tetrahydrofuran under nitrogen is cooled in a dry ice-acetone bath to -78° C. and 19-hydroxy-5α-androstane-3,17-dione acetate is slowly added. The reaction mixture is stirred for 2 hours at this temperature, warmed to 0° C. and stirring continued for an additional two hours. The reaction mixture is decomposed by the addition of 3 N sodium hydroxide solution followed by a 30% hydrogen peroxide solution. Solid potassium carbonate is added to this mixture and the tetrahydrofuran decanted therefrom. The solid residue is washed with fresh tetrahydrofuran and the combined tetrahydrofuran solutions are dried over anhydrous sodium sulfate, filtered, and evaporated to dryness. The residue is crystallized from acetone to yield 5α-androstane-3α,17β,19-triol.
Workup
- stirringstirring
- waitcontinued for an additional two hours
- customthe tetrahydrofuran decanted
- washThe solid residue is washed with fresh tetrahydrofuran
- dry with materialthe combined tetrahydrofuran solutions are dried over anhydrous sodium sulfate
- filtrationfiltered
- customevaporated to dryness
- customThe residue is crystallized from acetone
Sources & evidence
- ORD record
- ord-4d5dc3f722d848a3b4621510d303f74f
- Source dataset
- uspto-grants-1978_01
- Patent number
- US04071625
Reaction notes
Loading…