Diisopropylamine → HCID 68899458, compound

HRID 523587Notes

Reaction equation

HRID 523587 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[C:8]1(=[O:12])[CH2:11][CH2:10][CH2:9]1.C([Li])CCC.C(NC(C)C)(C)C>C1COCC1>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]1([OH:12])[CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 122863-BromopyridineHCID 14496CyclobutanoneHCID 178418339Butyllithium

Product 1

HCID 68899458HCID 68899458, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-bromopyridine (1 g, 6.329 mmol) was reacted with cylcobutanone (0.93 mL, 6.369 mmol), n-butyl lithium (4.02 mL, 7.64 mmol) and diisopropyl amine (0.99 mL, 7.005 mmol) in dry THF to afford the crude product. Purification by column chromatography on silica gel (40% ethyl acetate in hexane) afforded 802 mg of the product (55% yield). LCMS Purity: 79%, m/z=227.9 (M+1)

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b19ebe027a2343b88a28a1689e7387cc
Source dataset
uspto-grants-2016_05
Patent number
US09339501B2

Reaction notes

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