Sodium Hydroxide → HCID 56978869, compound

HRID 1941189Notes

Reaction equation

HRID 1941189 reaction equation
C(OCO[C@H:6]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@@H:8]([C:9](=[O:35])[CH2:10][C@@H:11]3[C@@H:29]2[CH2:28][CH2:27][C@@:26]2([CH3:34])[C@H:12]3[CH2:13][C@@H:14]3[O:19][C@@:18]4([O:25][CH2:24][C@H:22]([CH3:23])[CH2:21][CH2:20]4)[C@@H:16]([CH3:17])[C@@H:15]32)[CH2:7]1)C.[OH-].[Na+]>Cl.CO.O1CCCC1>[CH3:17][C@@H:16]1[C@:18]2([O:25][CH2:24][CH:22]([CH3:23])[CH2:21][CH2:20]2)[O:19][C@H:14]2[CH2:13][C@@H:12]3[C@@:26]([CH3:34])([C@@H:15]12)[CH2:27][CH2:28][C@H:29]1[C@H:11]3[CH2:10][C:9](=[O:35])[CH:8]2[C@:30]1([CH3:33])[CH2:31][CH2:32][CH2:6][CH2:7]2

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 53719778HCID 53719778, compound

Product 1

HCID 56978869HCID 56978869, compoundYield 92.8%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
62 °C

Procedure

Concentrated hydrochloric acid (2 drops) was added to a solution of (3β,5α,25R)-3-ethoxymethoxy-spirostan-6-one (0.70 g, 1.43 mmol) in methanol (10 mL) and tetrahydrofuran (10 mL). The mixture was stirred under nitrogen atmosphere and heated to 62° C. After 15 minutes, the reaction was cooled to 0° C. and neutralized with 15% sodium hydroxide solution. The mixture was concentrated in vacuo then diluted with ethyl acetate. The organic layer was washed with water (2×), brine (1×), dried (sodium sulfate), concentrated in vacuo and purified by flash chromatography (1:1 hexane/ethyl acetate) to afford 0.55 g (89.4%) of the title compound as a colorless solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionthen diluted with ethyl acetate
  3. washThe organic layer was washed with water (2×), brine (1×)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-dca203584d8641a396f9d667c6348860
Source dataset
uspto-grants-1997_12
Patent number
US05703052

Reaction notes

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