Hydrochloric Acid → HCID 22797504, compound

HRID 2397623Notes

Reaction equation

HRID 2397623 reaction equation
[C:1]([BH3-])#[N:2].[Na+].[CH2:5]([O:12][C@@H:13]([CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH2:14]C=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Br-].[NH4+].Cl>CO>[NH2:2][CH2:1][CH2:14][C@@H:13]([O:12][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25514Ammonium BromideHCID 5003444Sodium cyanoborohydrideHCID 22797509HCID 22797509, compound

Product 1

HCID 22797504HCID 22797504, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium cyanoborohydride (5% excess over theoretical amount) is allowed portionwise over 1/2 hour to a stirred mixture of 3-(S)-benzyloxy-1-octanal (1 molar equivalent) and ammonium bromide (15 molar equivalents) in methanol at room temperature. The resulting reaction mixture is stirred at room temperature for 48 hours, then is cooled to 0° to 5° C. and cautiously treated with concentrated hydrochloric acid to destroy excess hydride reagent. The resulting reaction mixture is evaporated in vacuo at or below 40° C. leaving a residual mass which is partitioned between 5% hydrochloric acid and ether. The aqueous phase is separated, slowly basicified with potassium carbonate, and extracted with ether three times. The combined organic extract is washed with saturated aqueous brine, dried over sodium sulfate, and filtered. In vacuo evaporation of the filtrate leaves the title compound as an essentially colorless oil.

Workup

  1. customThe resulting reaction mixture
  2. temperatureis cooled to 0° to 5° C.
  3. customto destroy excess hydride reagent
  4. customThe resulting reaction mixture
  5. customis evaporated in vacuo at or below 40° C.
  6. customleaving a residual mass which
  7. customis partitioned between 5% hydrochloric acid and ether
  8. customThe aqueous phase is separated
  9. extractionextracted with ether three times
  10. extractionThe combined organic extract
  11. washis washed with saturated aqueous brine
  12. dry with materialdried over sodium sulfate
  13. filtrationfiltered
  14. customIn vacuo evaporation of the filtrate

Sources & evidence

ORD record
ord-058384c56c944f68b8dca51b42e5c879
Source dataset
uspto-grants-1977_05
Patent number
US04022794

Reaction notes

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