Sodium borohydride → HCID 57750366, compound

HRID 423065Notes

Reaction equation

HRID 423065 reaction equation
[BH4-].[Na+].[NH2:3][C@H:4]([C:10]1[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=1)[CH2:5][C:6](OC)=[O:7]>CO>[NH2:3][C@H:4]([C:10]1[CH:11]=[CH:12][C:13]([C:16]#[N:17])=[CH:14][CH:15]=1)[CH2:5][CH2:6][OH:7]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 26594785(S)-methyl 3-amino-3-(4-cyanophenyl)propanoate

Product 1

HCID 57750366HCID 57750366, compoundYield 19.13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

Sodium borohydride (1.039 mL, 29.48 mmol) was added portionwise to (S)-methyl 3-amino-3-(4-cyanophenyl)propanoate (2.23 g, 10.92 mmol) in methanol (20 mL) at 0° C. over a period of 5 minutes. The resulting solution was stirred at 20° C. for 24 hours. The reaction mixture was quenched with saturated NaHCO3 (50 mL), extracted with EtOAc (3×100 mL), the organic layer was washed with saturated brine (75 mL), dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 8% MeOH with ammonia in DCM. Pure fractions were evaporated to dryness to afford (S)-4-(1-amino-3-hydroxypropyl)benzonitrile (0.368 g, 19.13%) as a colourless oil.

Workup

  1. customThe reaction mixture was quenched with saturated NaHCO3 (50 mL)
  2. extractionextracted with EtOAc (3×100 mL)
  3. washthe organic layer was washed with saturated brine (75 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto afford crude product
  8. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 8% MeOH with ammonia in DCM
  9. customPure fractions were evaporated to dryness

Sources & evidence

ORD record
ord-7558e904fec94fc28f38cd91b0148040
Source dataset
uspto-grants-2012_01
Patent number
US08101623B2

Reaction notes

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