Sodium Hydroxide → HCID 86750802, compound

HRID 1585515Notes

Reaction equation

HRID 1585515 reaction equation
BrC1C[C@@H](C)CO[C@@]21[C@@H](C)[C@@H]1[C@]3(C)[C@@H](C[C@@H]1O2)[C@H]1[C@@H]([C@]2(C)[C@@H](CC1)C[C@@H](O)CC2)[C@@H](O)[C@@H]3O.[Br:34][CH:35]1[CH2:71][C@@H:70]([CH3:72])[CH2:69][O:68][C@@:36]21[C@@H:40]([CH3:41])[C@@H:39]1[C@:42]3([CH3:67])[C@@H:55]([CH2:56][C@@H:38]1[O:37]2)[C@H:54]1[C@@H:45]([C@:46]2([CH3:58])[C@@H:51]([CH2:52][CH2:53]1)[CH2:50][C@@H:49]([OH:57])[CH2:48][CH2:47]2)[C@@H:44](O)[C@@H:43]3[O:60]C(=O)C(Cl)(Cl)Cl.[OH-].[Na+]>O.C(O)C>[Br:34][CH:35]1[CH2:71][C@@H:70]([CH3:72])[CH2:69][O:68][C@@:36]21[C@@H:40]([CH3:41])[C@@H:39]1[C@:42]3([CH3:67])[C@@H:55]([CH2:56][C@@H:38]1[O:37]2)[C@H:54]1[C@@H:45]([C@:46]2([CH3:58])[C@@H:51]([CH2:52][CH2:53]1)[CH2:50][C@@H:49]([OH:57])[CH2:48][CH2:47]2)[C@H:44]1[O:60][C@@H:43]31

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 53655626HCID 53655626, compoundHCID 54097936HCID 54097936, compound

Product 1

HCID 86750802HCID 86750802, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The following procedure is a variation of that described in Helv. Chim. Act., 1953, 36, 1241. (3β,5α,11α,12β,25R)-11,23-dibromospirostan-3,12-diol (18.08 g) was dissolved in pyridine (500 mL) at room temperature and treated with silver oxide (70.0 g). The resulting mixture was stirred in the dark for 71 hours. The mixture was filtered and the solid washed with ether and then chloroform. These washes were combined with the filtrate and concentrated. The resulting solid was purified by flash chromatography (1:1 hexane:ethyl acetate) to give 12.2 g of a 1:1 mixture of the title compound and (3β,5α,25R)-23-bromospirostan-3-ol-12-one. Further chromatography (7:3 hexane:ethyl acetate) provides pure title compound. (3β,5α,11β,12α,25R)-23-bromo-12-(trichloroacetoxy)spirostan-3,11 -diol: Using the procedure described in J. Chem. Soc., 1956, 4330, (3β,5α, 11β,12β,25R)-23-bromo-11,12-epoxyspirostan-3-ol was treated with trichloroacetic acid in toluene at room temperature for 3 days to give the title compound. (3β,5α, 11β,12α,25R)-23-bromo-spirostan-3,11,12-triol: Using the procedure described in J. Chem. Soc., 1956, 4330, (3β,5α,11β,12α,25R)-23-bromo-12-(trichloroacetoxy)spirostan-3,11-diol was saponified with sodium hydroxide in water and ethanol to give the title compound.

Sources & evidence

ORD record
ord-a671d0fd54ac4ed4830dd078f73de3d3
Source dataset
uspto-grants-1999_08
Patent number
US05939398

Reaction notes

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