(R)-1,2-Epoxypropane → HCID 23434290, compound

HRID 2121870Notes

Reaction equation

HRID 2121870 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[C:5]([CH3:16])[CH:4]=1.[Li]CCCC.[CH2:22]1[O:25][C@@H:23]1[CH3:24]>C1COCC1>[OH:25][CH:23]([CH3:24])[CH2:22][CH2:16][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[NH:9][C:10](=[O:15])[C:11]([CH3:12])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 146261(R)-1,2-EpoxypropaneHCID 15414709N-(4-Methoxy-2-methylphenyl)-2,2-dimethylpropanamideHCID 178418339Butyllithium

Product 1

HCID 23434290HCID 23434290, compoundYield 106.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of the the product from Step A (3.00 g, 13.6 mmol) at 0° C. in anhydrous THF (50 mL) was added a solution of 2.5 M n-BuLi in hexanes (13.6 mL, 2.5 equiv.) over about 2 min under a nitrogen atmosphere. After 10 minutes a solution of (R)-propylene oxide (1.18 g, 1.5 eq) in anhydrous THF (5 mL) was added and the mixture was stirred for about 30 min. The reaction was quenched by the addition of ice-water. The THF was evaporated and the residue was extracted with ethyl acetate to give a viscous oil (4.03 g), which was used in next reaction without further purification: LC/MS (+APCI) m/z 280 (M+H).

Workup

  1. customThe reaction was quenched by the addition of ice-water
  2. customThe THF was evaporated
  3. extractionthe residue was extracted with ethyl acetate

Sources & evidence

ORD record
ord-517708e15ea149308d8e19ef658fa98c
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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