Sodium borohydride → HCID 69231625, compound

HRID 1181110Notes

Reaction equation

HRID 1181110 reaction equation
[C:1]([O:5][C:6](=[O:31])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:21][CH:22]=2)=[CH:11][C:10]=1[CH:29]=[O:30])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6](=[O:31])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[O:21][CH:22]=2)=[CH:11][C:10]=1[CH2:29][OH:30])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86621485HCID 86621485, compound

Product 1

HCID 69231625HCID 69231625, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100 mL round bottomed flask was charged with 3-{2-formyl-4-[2-(2-phenyloxazol-4-yl)ethoxy]phenyl}propionic acid tert-butyl ester (1.82 g, 4.18 mmol) and absolute ethanol (20 mL). The stirring solution was cooled in an ice/ethanol bath and treated with sodium borohydride (0.31 g, 8.36 mmol). The cold bath was removed, and the mixture was stirred at ambient temperature under a nitrogen atmosphere for 2 h. The reaction mixture was poured into EtOAc (100 mL) and ice water (100 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated to a yellow oil (1.62 g, 88%). 1H NMR (400 MHz, CDCl3) δ 1.38 (s, 9H), 2.37 (s, 3H), 2.54 (t, J=7.6 Hz, 2H), 2.88 (t, J=7.6 Hz, 2H), 2.97 (t, J=6.6 Hz, 2H), 4.23 (t, J=6.6 Hz, 2H), 4.66 (s, 2H), 6.78 (dd, J=8.3, 2.9 Hz, 1H), 6.94 (d, J=2.4 Hz, 1H), 7.09 (d, J=8.3 Hz, 1H), 7.38-7.45 (m, 3H), 7.97 (dd, J=8.1, 1.7 Hz, 2H). MS (ES) m/e 438 (M+1).

Workup

  1. temperatureThe stirring solution was cooled in an ice/ethanol bath
  2. customThe cold bath was removed
  3. additionThe reaction mixture was poured into EtOAc (100 mL) and ice water (100 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to a yellow oil (1.62 g, 88%)

Sources & evidence

ORD record
ord-90eba8369f284b92a12a0dbd4cd5cdf9
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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