Sodium borohydride → HCID 22625979, compound

HRID 277763Notes

Reaction equation

HRID 277763 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C:11](=[O:28])[N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+]>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([CH2:19][C:20]3[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=3)[C:11](=[O:28])[NH:10]2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22625969HCID 22625969, compound

Product 1

HCID 22625979HCID 22625979, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a 0° C. solution of 9 (9.33 g, 24.6 mmol) in dioxane (250 mL) was added NaBH4 (1.02 g, 27.1 mmol) in one portion. The solution stirred for two hours at room temperature. The solvent was removed in vacuo, and the residue was partitioned between CHCl3 and 1 N HCl. The aqueous layer was extracted with CHCl3, and the combined organic extracts were dried, concentrated, and purified by PCTLC (1:1 EtOAc:Hex). A white solid was obtained. 1H NMR (CDCl3, 400 MHz) 7.30-7.04 (m, 6H), 6.93-6.83 (m, 6H), 5.58 (s, 1H), 5.18-5.04 (q, 2H), 3.77 (s, 3H).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between CHCl3 and 1 N HCl
  3. extractionThe aqueous layer was extracted with CHCl3
  4. customthe combined organic extracts were dried
  5. concentrationconcentrated
  6. custompurified by PCTLC (1:1 EtOAc:Hex)
  7. customA white solid was obtained

Sources & evidence

ORD record
ord-17ae3241794c4f67add2160d25c5d38e
Source dataset
uspto-grants-2002_03
Patent number
US06358959B1

Reaction notes

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