Sodium borohydride → HCID 67482540, compound

HRID 1817764Notes

Reaction equation

HRID 1817764 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:23]=[CH:22][C:9]([C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:11])=[CH:8][CH:7]=1)(=[O:5])[CH3:4]>CO>[OH:5][CH:3]([C:6]1[CH:23]=[CH:22][C:9]([C:10]([NH:12][CH2:13][CH2:14][C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])=[O:11])=[CH:8][CH:7]=1)[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67482692HCID 67482692, compound

Product 1

HCID 67482540HCID 67482540, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (0.28 g, 7.4 mmol) was added as solid to a solution of tert-butyl N-(4-acetylbenzoyl)-β-alaninate (2.11 g, 7.24 mmol) in MeOH (50 ml). After stirring at room temperature for 30 min, the reaction was quenched by adding ethyl acetate (150 ml) and 2N HCl (50 ml). The organic layer was washed with 1 NHCl 2×, brine 2×, and dried over Na2SO4. Evaporation of solvent and vacuum drying afforded tert-butyl N-[4-(1-hydroxyethyl)benzoyl]-β-alaninate as a colorless oil. NMR (CDCl3) δ: 1.46 (s, 9H); 1.49 (d, J=6.6 Hz, 3H); 2.55 (t, J=6.0 Hz, 2H); 3.67 (q, J=6.0 Hz, 2H); 4.94 (q, J=6.6 Hz, 1H); 6.88 (br, 1H); 7.42 (d, J=8.2 Hz, 2H); 7.72 (d, J=8.2 Hz, 2H). MS C16H23NO4 Cald: 293.16; Obsd: (M+Na) 316.12.

Workup

  1. customthe reaction was quenched
  2. additionby adding ethyl acetate (150 ml) and 2N HCl (50 ml)
  3. washThe organic layer was washed with 1 NHCl 2×, brine 2×
  4. dry with materialdried over Na2SO4
  5. customEvaporation of solvent and vacuum
  6. customdrying

Sources & evidence

ORD record
ord-6417492fe1374e9b8d51c3f0172ba7aa
Source dataset
uspto-grants-2009_10
Patent number
US07598285B2

Reaction notes

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