Sodium borohydride → HCID 18998207, compound

HRID 1180106Notes

Reaction equation

HRID 1180106 reaction equation
[C:1]([O:5][C:6]([CH2:8]/[N:9]=[CH:10]/[C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]([CH2:8][NH:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178497923HCID 178497923, compound

Product 1

HCID 18998207HCID 18998207, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example D (8.5 g, 30 mmol) in MeOH (80 mL) was slowly added solid NaBH4 (3.42 g, 90 mmol) while the reaction temperature was controlled below 20° C. After stirring for 2 h, the reaction was quenched with H2O, extracted with EtOAc (3×100 mL) and the combined organic layers were washed with brine, dried (Na2SO4), concentrated in vacuo. The residue was purified via flash column chromatography to yield methyl 4-(((t-butoxycarbonyl)methylamino)methyl)benzoate (6.55 g, 77% yield). 1H NMR (CDCl3) δ 7.98 (d, J=8.4 Hz, 2H), 7.40 (d, J=8.4 Hz, 2H), 3.90 (s, 3H,) 3.84 (s, 2H) 3.29 (s, 2H) 1.46 (s, 9H).

Workup

  1. customwas controlled below 20° C
  2. customthe reaction was quenched with H2O
  3. extractionextracted with EtOAc (3×100 mL)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via flash column chromatography

Sources & evidence

ORD record
ord-fa303dd3d2164d519d781b2bc703333b
Source dataset
uspto-grants-2007_10
Patent number
US07279576B2

Reaction notes

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