Sodium borohydride → HCID 9884000, compound

HRID 1108558Notes

Reaction equation

HRID 1108558 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:15]2[CH2:19][CH:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][N:16]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][C:10]([CH:13]=[O:14])=[CH:9]1.[BH4-].[Na+]>CO.[OH-].[Na+]>[F:1][C:2]1[CH:3]=[C:4]([C:15]2[CH2:19][CH:18]([CH2:20][NH:21][C:22](=[O:24])[CH3:23])[O:17][N:16]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][C:10]([CH2:13][OH:14])=[CH:9]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 9905524HCID 9905524, compound

Product 1

HCID 9884000HCID 9884000, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

(-)-5-Acetamidomethyl-3-(3-fluoro-4-(3-formyl-pyrrol-1-yl)phenyl)isoxazoline (Example 15) (658 mg) is suspended/dissolved in 20 ml methanol under nitrogen. The mixture is treated with sodium borohydride (76 mg) and the reaction is stirred 1 hour at room temperature. The reaction is diluted with 1×10 ml 2N sodium hydroxide and the volatiles are removed in vacuo. The residue is diluted with 20 ml water and the white solid is collected and dried to give 609 mg of the title compound as an off white solid, mp 162-164° C., [α]25D -72° (c 0.54, methanol).

Workup

  1. customthe volatiles are removed in vacuo
  2. additionThe residue is diluted with 20 ml water
  3. customthe white solid is collected
  4. customdried

Sources & evidence

ORD record
ord-4c37fb64d22a4a379891614344a2d804
Source dataset
uspto-grants-2000_05
Patent number
US06069141

Reaction notes

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