Sodium borohydride → HCID 57810575, compound

HRID 2106468Notes

Reaction equation

HRID 2106468 reaction equation
[CH3:1][C:2]([CH3:34])([CH3:33])[C:3](=[O:32])[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]=[C:24]([O:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:23]=[CH:22][C:20]=3[CH:21]=2)([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:31].[BH4-].[Na+]>C1COCC1>[CH2:13]([C:12]([C:17]1[O:18][C:19]2[CH:25]=[C:24]([O:26][S:27]([CH3:30])(=[O:29])=[O:28])[CH:23]=[CH:22][C:20]=2[CH:21]=1)([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:3]([OH:32])[C:2]([CH3:33])([CH3:34])[CH3:1])=[C:7]([CH3:31])[CH:8]=1)[CH2:15][CH3:16])[CH3:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57810567HCID 57810567, compound

Product 1

HCID 57810575HCID 57810575, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methanesulfonic acid 2-{1-[4-(3,3-dimethyl-2-oxo-butoxy)-3-methyl-phenyl]-1-ethyl-propyl}-benzofuran-6-yl ester (34 mg, 0.069) in THF (5.0 mL) at 0° C. is treated with NaBH4 (13 mg, 0.349 mmol). The resulting mixture is stirred for 30 min at RT and quenched with HCl (1.0 N, 2.0 mL) and extracted with EtOAc (2×10 mL). The organic layer is dried over Na2SO4, concentrated to afford the title compound (30 mg, 88%).

Workup

  1. customquenched with HCl (1.0 N, 2.0 mL)
  2. extractionextracted with EtOAc (2×10 mL)
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-73d3ee8d41ba4d6bb731985aacd093c1
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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