Sodium borohydride → HCID 18511941, compound

HRID 1370813Notes

Reaction equation

HRID 1370813 reaction equation
[CH2:1]([N:8]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH:18]=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C.O1CCCC1>[CH2:20]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[CH2:18][OH:19])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 18511992HCID 18511992, compound

Product 1

HCID 18511941HCID 18511941, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product from Example 46A (1.5 g, 4.33 mmoles) in ethanol (10 mL) and tetrahydrofuran (4 mL) was treated with sodium borohydride (0.164 g, 4.33 mmoles). After stirring for 30 minutes at room temperature, the mixture was quenched with saturated ammonium chloride and diluted with diethyl ether. The diethyl ether was washed with saturated ammonium chloride, brine, dried with sodium sulfate, filtered and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 10:1 to 4:1 hexanes:ethyl acetate) to provide the title compound (1.39 g, 92%). MS (ESI+) m/z 348 (M+H)+.

Workup

  1. customthe mixture was quenched with saturated ammonium chloride
  2. additiondiluted with diethyl ether
  3. washThe diethyl ether was washed with saturated ammonium chloride, brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was purified by flash chromatography (silica gel, 10:1 to 4:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-ee4bfb3d52da405580fb132711370747
Source dataset
uspto-grants-2003_06
Patent number
US06583180B2

Reaction notes

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