Sodium hydride → HCID 67885528, compound

HRID 1032082Notes

Reaction equation

HRID 1032082 reaction equation
[H-].[Na+].[C:3]([OH:8])(=[O:7])[C:4]([OH:6])=[O:5].[C:9]1([CH:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:16]2[CH2:19][C@@H:18]([OH:20])[C@@H:17]2[CH3:21])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[H][H].F[C:31]1[CH:32]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:34]=[CH:35][CH:36]=1>CN(C=O)C>[C:3]([OH:8])(=[O:7])[C:4]([OH:6])=[O:5].[C:22]1([CH:15]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:16]2[CH2:19][C@@H:18]([O:20][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=3)[C@@H:17]2[CH3:21])[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 67867alpha,alpha,alpha,3-TetrafluorotolueneHCID 67885458HCID 67885458, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67885528HCID 67885528, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A stirred slurry of 1.2 g (0.03 mole) of sodium hydride (60% dispersion in mineral oil) in 50 ml of dry DMF was treated with 3.45 g (0.01 mole) of trans-1-diphenylmethyl-2-methylazetidin-3-ol oxalate added in small portions. When the addition was complete and the evolution of hydrogen ceased, the reaction was heated to 80° C. for 2 hr then 1.64 g (0.01 mole) of 3-fluoro-trifluoromethylbenzene was added dropwise. The reaction mixture was stirred at 80° C. for an additional 18 hr. The reaction mixture was diluted with ice water and extracted with 3×25 ml of toluene. The extracts were combined, dried over magnesium sulfate, filtered, and the filtrate treated with 1 g of oxalic acid. The resulting solid was collected by filtration. Recrystallization from acetone-isopropyl ether yielded 2.2 g (4.5%) of fine white crystals, m.p. 146°-147° C. Proton NMR shows it to be the trans compound.

Workup

  1. additionadded in small portions
  2. additionWhen the addition
  3. extractionextracted with 3×25 ml of toluene
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. additionthe filtrate treated with 1 g of oxalic acid
  7. filtrationThe resulting solid was collected by filtration
  8. customRecrystallization from acetone-isopropyl ether

Sources & evidence

ORD record
ord-ecc6381f2f314d508272005b0403a25b
Source dataset
uspto-grants-1990_09
Patent number
US04956359

Reaction notes

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