Sodium borohydride → HCID 66704434, compound

HRID 426041Notes

Reaction equation

HRID 426041 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:27])[CH2:9][CH2:10][CH:11]([C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[CH3:26])[O:12][CH2:13][C:14](OCC)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[Cl:25][C:23]1[CH:22]=[CH:21][C:20]([CH3:26])=[C:19]([CH:11]([O:12][CH2:13][CH2:14][OH:15])[CH2:10][CH2:9][N:8]([CH3:27])[C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2])[CH:24]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59364365HCID 59364365, compound

Product 1

HCID 66704434HCID 66704434, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(3-(tert-butoxycarbonyl(methyl)amino)-1-(5-chloro-2-methylphenyl) propoxy)acetate (800 mg, 2 mmol) in MeOH (16 mL) was added NaBH4 (305 mg, 8 mmol) in portions while the temperature was lower than 40° C. After addition, the mixture was stirred at room temperature for 2-3 h. The solvent was removed in vacuo to the residue, which was partitioned between water and ethyl acetate. The organic layer was washed with H2O and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified on silica gel chromatography to afford tert-butyl 3-(5-chloro-2-methylphenyl)-3-(2-hydroxyethoxy)propyl(methyl)carbamate (400 mg, 56%). 1H NMR (CDCl3, 400 MHz) δ 1.22 (m, 3H), 1.43 (m, 9H), 1.87 (m, 2H), 2.21 (s, 3H), 2.87 (s, 3H), 3.39 (m, 2H), 3.80 (m, 1H), 4.00 (m, 1H), 4.61 (m, 1H), 7.08 (m, 2H), 7.37 (m, 1H).

Workup

  1. customwas lower than 40° C
  2. additionAfter addition
  3. customThe solvent was removed in vacuo to the residue, which
  4. customwas partitioned between water and ethyl acetate
  5. washThe organic layer was washed with H2O and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified on silica gel chromatography

Sources & evidence

ORD record
ord-151953a6a3184907a1aaf3936fffdeb8
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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