Nitrogen → HCID 23117115, compound

HRID 1921268Notes

Reaction equation

HRID 1921268 reaction equation
[C:1]12([C:11]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:16][C:15]=3F)=[N:12][OH:13])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.N#N.[H-].[Na+].O>CN(C=O)C>[C:1]12([C:11]3[C:14]4[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)=[CH:16][C:15]=4[O:13][N:12]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 4

HCID 947NitrogenHCID 962WaterHCID 24758Sodium hydrideHCID 86626349HCID 86626349, compound

Product 1

HCID 23117115HCID 23117115, compoundYield 94,550.102%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

1-adamantyl-(4-benzyloxy-2-fluorophenyl)methanone oxime (2.3 mg, 6 mM) in DMF (30 ml) was added at 0° C. dropwise under N2, to a stirred suspension of NaH (0.61 g, 18 mM, 60% oil dispersion) in DMF (10 ml). After the complete addition, the reaction mixture was allowed to warm to room temperature and poured into H2O. The precipitate was collected by filtration to give the expected product (2.06 g, 95%). mp 132° C.

Workup

  1. additionAfter the complete addition
  2. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-776e64d2f3544953be8f14f2dea94802
Source dataset
uspto-grants-2012_05
Patent number
US08173679B2

Reaction notes

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