Cyclopentanone → HCID 70982889, compound

HRID 572431Notes

Reaction equation

HRID 572431 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9]1.[Li]CCCC.C(N(C(C)C)CC)(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1([OH:13])[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 8452CyclopentanoneHCID 122863-BromopyridineHCID 81531DiisopropylethylamineHCID 178418339Butyllithium

Product 1

HCID 70982889HCID 70982889, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Using analogous reaction condition and reagents as described in Example 20 for the preparation of I-20a above, 3-bromo pyridine solution (1.0 g, 6.36 mmol) was reacted with cyclopentanone solution (0.6 mL, 7.0 mmol) in dry THF (6 mL), n-BuLi solution (4.0 mL, 7.6 mmol) and diisopropylethyl amine (1.0 mL, 7.0 mmol) in dry THF (6 mL) to afford the crude product. The crude was purified by column chromatography on silica gel (20% ethyl acetate in hexane) afforded 520 mg of the product (34% yield).

Workup

  1. customto afford the crude product
  2. customThe crude was purified by column chromatography on silica gel (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-9bfec88505104a4f8e558335751e7038
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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