2,4-Difluoronitrobenzene → HCID 58421532, compound

HRID 406059Notes

Reaction equation

HRID 406059 reaction equation
[CH3:1][C:2]([O:5][C:6]([NH:8][C@@H:9]1[C@@H:13]([OH:14])[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])[CH3:3].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.F[C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[N+:33]([O-:35])=[O:34]>C1COCC1.O>[C:2]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][CH2:12][C@@H:13]1[O:14][C:26]1[CH:31]=[C:30]([F:32])[CH:29]=[CH:28][C:27]=1[N+:33]([O-:35])=[O:34])([CH3:1])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 679672,4-DifluoronitrobenzeneHCID 2733832Lithium HexamethyldisilazideHCID 10104271tert-Butyl [(1S,2S)-2-hydroxycyclopentyl]carbamate

Product 1

HCID 58421532HCID 58421532, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

(1S,2S)-trans-N-boc-2-aminocyclopentanol was dissolved in 50 ml THF and cooled to 10° C. To the reaction mixture were added 32.2 ml LiHMDS 1M in THF. After 1 hour 2.72 ml 2,4-difluoronitrobenzol were added and the mixture was stirred at rt overnight. Then the mixture was poured in water and extracted with ethylacetate. The organic layer was washed with water, dried and concentrated in vacuo.

Workup

  1. extractionextracted with ethylacetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-12a2ae7edcfd47aeb5df371811bec19e
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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