Sodium borohydride → HCID 11338078, compound

HRID 267151Notes

Reaction equation

HRID 267151 reaction equation
[Cl:1][CH2:2][C:3](=[O:27])[C@@H:4]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1.[BH4-].[Na+]>O1CCCC1>[Cl:1][CH2:2][C@@H:3]([OH:27])[C@@H:4]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 7019693HCID 7019693, compound

Product 1

HCID 11338078HCID 11338078, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The foregoing benzyl [3-chloro-1(S)-[(2-naphthyl)methyl]-2-oxopropyl]carbamate was dissolved in 100 ml of 10% aqueous tetrahydrofuran, cooled to 0° C. and treated with 0.456 g of sodium borohydride which was added carefully as the solid. The mixture was stirred at 0° C. for 1 hour and then at room temperature overnight. The mixture was evaporated to give a white solid which was partitioned between dichloromethane and water. The stirred mixture was carefully acidified to pH 1 with concentrated hydrochloric acid. The phases were separated and the aqueous phase was back-extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulphate and evaporated to give 4.325 g of crude product of melting point 155°-160° C. This crude product was extracted with boiling n-hexane. After removal of the solvent by evaporation the residue was recrystallized from ethyl acetate/n-hexane to give 1.046 g of pure benzyl [3-chloro-2(S)-hydroxy-1(S)-[(2-naphthyl)methyl]propyl]carbamate of melting point 173°-174° C.

Workup

  1. additionwas added carefully as the solid
  2. customat room temperature
  3. customovernight
  4. customThe mixture was evaporated
  5. customto give a white solid which
  6. customwas partitioned between dichloromethane and water
  7. customThe phases were separated
  8. extractionthe aqueous phase was back-extracted with dichloromethane
  9. dry with materialThe combined organic phases were dried over anhydrous sodium sulphate
  10. customevaporated
  11. customto give 4.325 g of crude product of melting point 155°-160° C
  12. extractionThis crude product was extracted with boiling n-hexane
  13. customAfter removal of the solvent
  14. customby evaporation the residue
  15. customwas recrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-0339238a4c024c2a89bb832ae05884cc
Source dataset
uspto-grants-1997_07
Patent number
US05652369

Reaction notes

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