HCID 13891111, compound → (3S,4S)-3-Hydroxy-4-amino-5-cyclohexyl-1-pentene

HRID 373641Notes

Reaction equation

HRID 373641 reaction equation
[CH:1]1([CH2:7][C@H:8]2[CH:12]([CH:13]=[CH2:14])[O:11]C(=O)[NH:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>O1CCOCC1.O>[OH:11][C@H:12]([C@@H:8]([NH2:9])[CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH:13]=[CH2:14]

Participants

5

Reactant 2

HCID 13891111HCID 13891111, compoundHCID 17749109Barium hydroxide, octahydrate

Product 1

HCID 14478714(3S,4S)-3-Hydroxy-4-amino-5-cyclohexyl-1-pentene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To the resultant 5S-diastereomer from Example 4 (2.06 g, 9.84 mmol) in dioxane (180 ml) and water (120 ml) was added barium hydroxide octahydrate (6.24 g, 19.8 mmol). The mixture was refluxed for 18 h, cooled, filtered, concentrated, taken up in water and extracted with ethyl acetate which was dried over Na2SO4 and evaporated to afford 1.64 9 (91%) of the desired product, m.p.: 59°-61° C.

Workup

  1. temperatureThe mixture was refluxed for 18 h
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationconcentrated
  5. extractionextracted with ethyl acetate which
  6. dry with materialwas dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-d221a7cb9bae4fc09a44956c6d96a3ae
Source dataset
uspto-grants-1992_11
Patent number
US05164388

Reaction notes

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