Sodium borohydride → HCID 59364372, compound

HRID 426039Notes

Reaction equation

HRID 426039 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([C:8](=[O:20])[CH2:9][CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:7]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:21])=[C:6]([CH:8]([OH:20])[CH2:9][CH2:10][N:11]([CH3:19])[C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16])[CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59364349HCID 59364349, compound

Product 1

HCID 59364372HCID 59364372, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 3-(5-chloro-2-methylphenyl)-3-oxopropyl(methyl)carbamate (1.3 g, 4.2 mmol) in MeOH (26 mL) was added NaBH4 (0.64 g, 16.7 mmol) in portions. After addition, the mixture was stirred at room temperature overnight. The solvent was removed in vacuo to the residue, which was portioned between water and EtOAc. The organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. 1H NMR (CDCl3, 400 MHz) δ 1.49 (s, 9H), 1.65 (s, 3H), 1.94 (m, 2H), 2.87 (s, 3H), 7.26 (m, 4H).

Workup

  1. additionAfter addition
  2. customThe solvent was removed in vacuo to the residue, which
  3. washThe organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c8428890e4894543bc311eb84f593767
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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