p-Toluenesulfonic acid → HCID 69905541, compound

HRID 582519Notes

Reaction equation

S(NN=[C:13]1[CH2:18][CH2:17][C@H:16]2[C@H:19]3[C@H:29]([CH2:30][CH2:31][C@:14]12[CH3:15])[C@:27]1([CH3:28])[C@H:22]([CH2:23][C@H:24]([OH:36])[C@@H:25]([O:32][CH:33]([CH3:35])[CH3:34])[CH2:26]1)[CH2:21][CH2:20]3)(C1C=CC(C)=CC=1)(=O)=O.[BH3-]C#N.[Na+].C1(C)C=CC(S(O)(=O)=O)=CC=1.S1(CCCC1)(=O)=O>O.CN(C=O)C>[CH:33]([O:32][C@H:25]1[CH2:26][C@@:27]2([CH3:28])[C@@H:22]([CH2:21][CH2:20][C@@H:19]3[C@@H:29]2[CH2:30][CH2:31][C@@:14]2([CH3:15])[C@H:16]3[CH2:17][CH2:18][CH2:13]2)[CH2:23][C@@H:24]1[OH:36])([CH3:35])[CH3:34]

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of 2β-isopropoxy-3α-hydroxy-5α-androstan-17-one tosylhydrazone (300 mg), NaBH3CN (144 mg) and p-toluenesulfonic acid (30 mg) was added DMF and sulfolane (1:1, 3 mL) and the mixture obtained was heated to 110° C. for 3 h. Then additional amount of NaBH3CN (144 mg) and p-toluenesulfonic acid (30 mg) was added and it was heated for another hour. Water was then added and the mixture was extracted with EtOAc (2×45 mL). The combined extracts were dried over Na2SO4 and the crude product obtained by removal of the solvent was purified by flash chromatography over silica gel to yield the pure 2β-isopropoxy-3α-hydroxy-5α-androstane (37 mg); TLC Rf (EtOAc:hexane 1:9)=0.17.

Workup

customthe mixture obtained
temperatureit was heated for another hour
extractionthe mixture was extracted with EtOAc (2×45 mL)
dry with materialThe combined extracts were dried over Na2SO4
customthe crude product obtained by removal of the solvent
customwas purified by flash chromatography over silica gel

Sources & evidence

ORD record: ord-d9281a591d1a4566b7bab6340deddc22
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05925630

Reaction notes

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