Hydrofluoric Acid → HCID 131720010, compound

HRID 1779941Notes

Reaction equation

HRID 1779941 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)[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]([OH:66])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[C:16](=[O:66])[C@@H:15]3[C@@:29]([CH3:43])([C@@H:18]12)[CH2:30][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 131720010HCID 131720010, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was synthesized from (3β,5α,11β,25R)-3-(t-butyidimethylsilyloxy)-11-(trimethylsilyloxy)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-ad146eecb5f64df696f4ec09ecd75c71
Source dataset
uspto-grants-1997_05
Patent number
US05629295

Reaction notes

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