Hydrochloric Acid → HCID 86733977, compound

HRID 1576331Notes

Reaction equation

HRID 1576331 reaction equation
[O:1]1[C@@:15]23[C@:6]4([CH2:18][CH2:17][N:16](C(=O)C(F)(F)F)[C@@H:14]2[CH2:13][C:12]2[CH:11]=[CH:10][C:9]([O:25][CH3:26])=[CH:8][C:7]4=2)[CH2:5][CH2:4][CH2:3][CH:2]13.[BH4-].[Na+].Cl>C(O)C>[O:1]1[C@@:15]23[C@:6]4([CH2:18][CH2:17][NH:16][C@@H:14]2[CH2:13][C:12]2[CH:11]=[CH:10][C:9]([O:25][CH3:26])=[CH:8][C:7]4=2)[CH2:5][CH2:4][CH2:3][CH:2]13

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86733978HCID 86733978, compound

Product 1

HCID 86733977HCID 86733977, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.0 g. (2.72 mmole) of the epoxide XXI and 0.103 g. (2.72 mmole) of sodium borohydride in 5 ml. of absolute ethanol was refluxed during 5 minutes. After cooling, the reaction mixture was acidified with dilute hydrochloric acid and then extracted with ether. The aqueous layer was separated and made alkaline by the addition of aqueous ammonia and then extracted with methylene chloride. The resulting extracts were dried over Na2SO4 and concentrated in vacuo to yield 800 mg. of an oil (XXII) which was not further purified but used directly in the next transformation. The IR and NMR spectra were consistent with the structure.

Workup

  1. additionA mixture of 1.0 g
  2. temperatureAfter cooling
  3. extractionextracted with ether
  4. customThe aqueous layer was separated
  5. additionby the addition of aqueous ammonia
  6. extractionextracted with methylene chloride
  7. dry with materialThe resulting extracts were dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customto yield 800 mg
  10. customof an oil (XXII) which was not further purified

Sources & evidence

ORD record
ord-52cadb923e764b3b9ac9ddd3b4e436a1
Source dataset
uspto-grants-1976_09
Patent number
US03980641

Reaction notes

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