5-Bromo-2-chloroanisole → 9-(4-Chloro-3-methoxyphenyl)-3-azaspiro[5.5]undec-8-ene

HRID 419279Notes

Reaction equation

HRID 419279 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:10])=[C:6]([O:8][CH3:9])[CH:7]=1.[Li]CCCC.C(OC([N:23]1[CH2:28][CH2:27][C:26]2([CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]2)[CH2:25][CH2:24]1)=O)(C)(C)C>C1COCC1>[Cl:10][C:5]1[CH:4]=[CH:3][C:2]([C:31]2[CH2:32][CH2:33][C:26]3([CH2:27][CH2:28][NH:23][CH2:24][CH2:25]3)[CH2:29][CH:30]=2)=[CH:7][C:6]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 27695675-Bromo-2-chloroanisoleHCID 51072194tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylateHCID 178418339Butyllithium

Product 1

HCID 160064329-(4-Chloro-3-methoxyphenyl)-3-azaspiro[5.5]undec-8-ene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Was prepared according to method A with the following variation: A solution of 5-bromo-2-chloroanisol (1.26 g, 5.7 mmol) in THF (7 mL) was added drop-wise to a solution of n-BuLi (1.6 M in hexanes (3.8 mL, 6.1 mmol)) at −78° C. and stirred for 30 min. A solution of 9-oxo-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (475 mg, 1.78 mmol) in THF (7 mL) was added. The mixture was stirred for 1 h. White solid. Mp. 182-185° C.

Workup

  1. customWas prepared
  2. stirringThe mixture was stirred for 1 h

Sources & evidence

ORD record
ord-0752added267418cafd8a8dc6cac1562
Source dataset
uspto-grants-2012_01
Patent number
US08093388B2

Reaction notes

Loading…