Lithium Hexamethyldisilazide → HCID 71117334, compound

HRID 2045792Notes

Reaction equation

HRID 2045792 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@H:9]2[CH2:13][CH2:12][CH2:11][C@H:10]2[C:14]([O:16]C)=O)=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:16])[C@@H:10]3[C@H:9]2[CH2:13][CH2:12][CH2:11]3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2733832Lithium HexamethyldisilazideHCID 71117304HCID 71117304, compound

Product 1

HCID 71117334HCID 71117334, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 500-mL, three-necked, round-bottomed flask was charged with cis-methyl 2-((4-fluorophenyl)amino)cyclopentanecarboxylate (racemic cis-17A′) (15.77 g, 66.5 mmol) and 75 mL of THF. The reaction mixture was cooled at 5° C. while a 1M solution of LiHMDS (73.1 mL, 73.1 mmol) was added dropwise via syringe over 10 min. The resulting reaction mixture was stirred at 5° C. to 15° C. for 1.5 h. The reaction mixture was then quenched into 200 mL of aqueous ammonium chloride and 250 mL of ethyl acetate. The organic layer was separated, washed with brine, dried over magnesium sulfate, filtered, and concentrated to give 14 g of cis-6-(4-fluorophenyl)-6-azabicyclo[3.2.0]heptan-7-one (racemic 17DP) as an orange oil.

Workup

  1. additionwas added dropwise via syringe over 10 min
  2. customThe resulting reaction mixture
  3. customThe reaction mixture was then quenched into 200 mL of aqueous ammonium chloride and 250 mL of ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bf0a012b0a5c4a51be4219a779f5cb06
Source dataset
uspto-grants-2013_11
Patent number
US08592383B2

Reaction notes

Loading…