Hydrofluoric Acid → HCID 22872545, compound

HRID 1941177Notes

Reaction equation

HRID 1941177 reaction equation
[Si]([O:8][C@H:9]1[CH2:35][CH2:34][C@@:33]2([CH3:36])[C@@H:11]([CH2:12][CH2:13][C@@H:14]3[C@@H:32]2[C@@H:31]([O:37][Si](C)(C)C)[C:30](=[O:42])[C@@:29]2([CH3:43])[C@H:15]3[CH2:16][C@@H:17]3[O:22][C@@:21]4([O:28][CH2:27][C@H:25]([CH3:26])[CH2:24][CH2:23]4)[C@@H:19]([CH3:20])[C@@H:18]32)[CH2:10]1)(C(C)(C)C)(C)C.F.C[C@@H]1[C@]2(OC[C@H](C)CC2)O[C@H]2C[C@@H]3[C@@](C)([C@@H]12)[C@H](O)C(=O)[C@H]1[C@H]3CC[C@@H]2[C@]1(C)CC[C@H](O)C2>C(#N)C>[CH3:20][C@@H:19]1[C@:21]2([O:28][CH2:27][C@H:25]([CH3:26])[CH2:24][CH2:23]2)[O:22][C@H:17]2[CH2:16][C@@H:15]3[C@@:29]([CH3:43])([C@@H:18]12)[C:30](=[O:42])[C@H:31]([OH:37])[C@H:32]1[C@H:14]3[CH2:13][CH2:12][C@@H:11]2[C@:33]1([CH3:36])[CH2:34][CH2:35][C@H:9]([OH:8])[CH2:10]2

Participants

5

Reactant 3

HCID 14917Hydrofluoric AcidHCID 15891086023-87-2HCID 54210416HCID 54210416, compound

Product 1

HCID 22872545HCID 22872545, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was synthesized from (3β,5α,11β,25R)-3-(t-butyldimethylsilyoxy)-11-(trimethylsilyoxy)spirostan-12-one was desilylated with hydrofluoric acid in acetonitrile according to the procedure described in J. Am. Chem. Soc., 1972, 94, 6190. The title compound must be carefully handled because it will rearrange to (3β,5α,12β,25R)-spirostan-3,12-diol-11-one if exposed to base.

Sources & evidence

ORD record
ord-2ca07e3ede394ab4b599e075215396df
Source dataset
uspto-grants-1997_12
Patent number
US05703052

Reaction notes

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