Diisopropylamine → HCID 68899458, compound

HRID 572429Notes

Reaction equation

HRID 572429 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-8f0516c6e5394c9eab896cc8de16d37c
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

Loading…