Water → HCID 18739877, compound

HRID 1934888Notes

Reaction equation

HRID 1934888 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C@H:10]3[C@H:15]4[CH2:16][C@H:12]([CH2:13][CH2:14]4)[C@H:11]3[C:17]([N:19]([CH3:21])[CH3:20])=[O:18])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[CH:22]([N-]C(C)C)(C)C.[Li+].IC.O>O1CCCC1>[CH3:22][C:2]1[S:1][C:5]2[CH:6]=[CH:7][C:8]([C@H:10]3[C@H:15]4[CH2:16][C@H:12]([CH2:13][CH2:14]4)[C@H:11]3[C:17]([N:19]([CH3:21])[CH3:20])=[O:18])=[CH:9][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 18739873HCID 18739873, compound

Product 1

HCID 18739877HCID 18739877, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (1S,2R,3S,4R)-3-(1-benzothien-5-yl)-N,N-dimethylbicyclo[2,2,1]heptane-2-carboxamide (200 mg, 0.67 mmol) in dry tetrahydrofuran (5 mL) at −78° C. was added lithium diisopropylamide (1.67 mL, 3.35 mmol). The mixture was stirred at this temperature for 1 hour before iodomethane (2.3 mL, 3.35 mmol) was added. The mixture was stirred for another 10 minutes at this temperature before it was allowed to warm to room temperature. After 1 hour, water was added and the layers were separated. The aqueous phase was extracted with ethyl acetate (2×10 mL) and the extracts were washed with water (2×10 mL) dried over magnesium sulphate and evaporated in-vacuo. Column chromatography with 20% ethyl acetate in hexane provided the (1S,2R,3S,4R)-3-(2-methyl-1-benzothien-5-yl)-N,N-dimethylbicyclo [2,2,1]heptane-2-carboxamide as a glass (140 mg, 66%). M/e 314 (M+H+).

Workup

  1. additionwas added
  2. waitAfter 1 hour
  3. customthe layers were separated
  4. extractionThe aqueous phase was extracted with ethyl acetate (2×10 mL)
  5. washthe extracts were washed with water (2×10 mL)
  6. dry with materialdried over magnesium sulphate
  7. customevaporated in-vacuo

Sources & evidence

ORD record
ord-6f14cc5a0dd7445a868a4ef3f0f88bc1
Source dataset
uspto-grants-2002_05
Patent number
US06384281B1

Reaction notes

Loading…