Sodium hydride → HCID 89463121, compound

HRID 1473267Notes

Reaction equation

HRID 1473267 reaction equation
[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:11]([C:12](=[O:20])[N:13]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH3:14])=[C:10]([C:21](OC)=[O:22])[C:9]3[CH2:25][O:26][CH2:27][CH2:28][C:8]2=3)=[CH:4][CH:3]=1.[H-].[Na+].[NH4+].[Cl-]>CN(C)C=O>[F:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:11]3[C:12](=[O:20])[N:13]([CH3:14])[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:21]([OH:22])[C:10]=3[C:9]3[CH2:25][O:26][CH2:27][CH2:28][C:8]2=3)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 89462891HCID 89462891, compound

Product 1

HCID 89463121HCID 89463121, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An ice cold solution of methyl 1-(4-fluorobenzyl)-2-((2-methoxy-2-oxoethyl)(methyl)carbamoyl)-1,4,6,7-tetrahydropyrano[4,3-b]pyrrole-3-carboxylate (3.2 g, 7.65 mmol) in N,N-Dimethylformamide (DMF) (38.2 ml) was treated with NaH (0.398 g, 9.94 mmol). After 5 min, the reaction mixture was warmed to ambient temperature. After 45 min, the reaction mixture was poured into sat. aq. NH4Cl and extracted with EtOAc. The organics were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to afford methyl 5-(4-fluorobenzyl)-9-hydroxy-7-methyl-6-oxo-1,3,4,5,6,7-hexahydropyrano[3′,4′:4,5]pyrrolo[2,3-c]pyridine-8-carboxylate (2.54 g, 6.57 mmol, 86% yield) as a yellow solid. LCMS (m/z) ES+=387 (M+1).

Workup

  1. waitAfter 45 min
  2. extractionextracted with EtOAc
  3. washThe organics were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9c32c0e7cb5f448b8c448d2f0c00633b
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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