Sodium borohydride → HCID 11711850, compound

HRID 1442689Notes

Reaction equation

HRID 1442689 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[C:3](=[O:30])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([C:17]2[O:18][C:19]3[CH:25]=[CH:24][C:23]([C:26]([OH:28])=[O:27])=[CH:22][C:20]=3[N:21]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:29].[BH4-].[Na+]>C1COCC1>[CH2:13]([C:12]([C:17]1[O:18][C:19]2[CH:25]=[CH:24][C:23]([C:26]([OH:28])=[O:27])=[CH:22][C:20]=2[N:21]=1)([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:3]([OH:30])[C:2]([CH3:31])([CH3:32])[CH3:1])=[C:7]([CH3:29])[CH:8]=1)[CH2:15][CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11597308HCID 11597308, compound

Product 1

HCID 11711850HCID 11711850, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-{1-[4-(3,3-Dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzooxazole-5-carboxylic acid (0.58 g, 1.33 mmol) in THF (30 mL) at RT is treated with NaBH4 (100 mg, 2.65 mmol). The resulting mixture is stirred for 1 h. The reaction is quenched with HCl (1.0 N, 5.0 mL) and extracted with EtOAc (3×50 mL). The organic layer is dried over Na2SO4 and concentrated to afford the title compound (0.58 g, 100%). MS (ES) m/e: 440.3 (M+1), 438.2 (M−1).

Workup

  1. customThe reaction is quenched with HCl (1.0 N, 5.0 mL)
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-65223af568584129a479e91807ecb2c9
Source dataset
uspto-grants-2010_02
Patent number
US07659296B2

Reaction notes

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