Sodium borohydride → HCID 53856751, compound

HRID 259828Notes

Reaction equation

HRID 259828 reaction equation
[CH2:1]([N:8]([C@H:16]([C:24](=[O:30])[CH2:25][CH2:26][CH:27]([CH3:29])[CH3:28])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.O1CCCC1>[CH2:1]([N:8]([C@H:16]([C@@H:24]([OH:30])[CH2:25][CH2:26][CH:27]([CH3:28])[CH3:29])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 53652452HCID 53652452, compound

Product 1

HCID 53856751HCID 53856751, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

2(S)-(N,N-Dibenzylamino)-1-phenyl-3-oxo-6-methylheptane (100 g) was dissolved in a mixture of methanol (500 ml) and tetrahydrofuran (500 ml), and the solution was cooled to -20° C. To the solution was portionwise added sodium borohydride (63 g) at said temperature. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure, and ethyl acetate (500 ml) and water (500 ml) were added to the residue for extraction. The water layer was re-extracted with ethyl acetate (250 ml ). The combined organic layer was washed with saturated brine (500 ml), and the organic layer was concentrated. Water (100 ml) was added to the residual oily substance, and azeotropic distillation was performed. After 8 times of azeotropic distillation, toluene (100 ml) was added. Additional azeotropic distillation gave 2(S)-(N,N-dibenzylamino)-1-phenyl-3(S)-hydroxy-6-methylheptane (56.8 g).

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure, and ethyl acetate (500 ml) and water (500 ml)
  3. additionwere added to the residue for extraction
  4. extractionThe water layer was re-extracted with ethyl acetate (250 ml )
  5. washThe combined organic layer was washed with saturated brine (500 ml)
  6. concentrationthe organic layer was concentrated
  7. additionWater (100 ml) was added to the residual oily substance, and azeotropic distillation
  8. distillationAfter 8 times of azeotropic distillation, toluene (100 ml)
  9. additionwas added
  10. distillationAdditional azeotropic distillation

Sources & evidence

ORD record
ord-8e7981f41b2544b998e66287ee6571af
Source dataset
uspto-grants-1996_06
Patent number
US05523410

Reaction notes

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