Hydrochloric Acid → HCID 18980505, compound

HRID 2392770Notes

Reaction equation

HRID 2392770 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[C:10]([OH:19])([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[CH2:9][CH2:8][C:7](=[O:20])[CH2:6]1)[CH3:3].[BH4-].[Na+].[ClH:23].[OH-].[Na+]>C(O)(C)C.O>[ClH:23].[CH3:3][N:2]([CH2:4][CH:5]1[CH2:6][CH:7]([OH:20])[CH2:8][CH2:9][C:10]1([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[OH:19])[CH3:1]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 18980499HCID 18980499, compound

Product 1

HCID 18980505HCID 18980505, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
10 °C

Procedure

10 g (36 mmole) of compound (66) were dissolved in 80 ml isopropanol and cooled to 10° C. 0.56 g (15 mmole) sodium borohydride were added with stirring. The mixture was then stirred for two hours at room temperature. Whilst cooling the mixture in an ice bath, 20 ml dilute hydrochloric acid were added (1:4 conc. HCl:H2O) followed by 10 ml of 20% aqueous sodium hydroxide solution. The product was extracted twice with dichloromethane. After drying and removal of the solvent by distillation, the crude product obtained (10.3 g) was dissolved in 2-butanone and was converted with trimethylchlorosilane/water into the hydrochloride for the separation of the diastereoisomers. 10.2 g (90% theoretical) of compound (68) crystallised out.

Workup

  1. stirringThe mixture was then stirred for two hours at room temperature
  2. temperatureWhilst cooling the mixture in an ice bath
  3. extractionThe product was extracted twice with dichloromethane
  4. customAfter drying
  5. customremoval of the solvent
  6. distillationby distillation

Sources & evidence

ORD record
ord-2ce12f6688814ad485b027f4b8e50e61
Source dataset
uspto-grants-1998_09
Patent number
US05801201

Reaction notes

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