p-Bromochlorobenzene → 9-(4-Chlorophenyl)-3-azaspiro[5.5]undec-8-ene

HRID 419278Notes

Reaction equation

HRID 419278 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][CH:3]=1.[Li]CCCC.C(OC([N:21]1[CH2:26][CH2:25][C:24]2([CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]2)[CH2:23][CH2:22]1)=O)(C)(C)C>C1COCC1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:29]2[CH2:30][CH2:31][C:24]3([CH2:25][CH2:26][NH:21][CH2:22][CH2:23]3)[CH2:27][CH:28]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 7806p-BromochlorobenzeneHCID 51072194tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylateHCID 178418339Butyllithium

Product 1

HCID 160064319-(4-Chlorophenyl)-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 4-bromochlorobenzene (1.15 g, 5.98 mmol) in THF (5 mL) was added drop-wise to a solution of n-BuLi (1.6 M in hexanes (4 mL, 6.4 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 (500 mg, 1.87 mmol) in THF (5 mL) was added. The mixture was stirred for 1 h. White solid Mp. 104.2-107.1° C.

Workup

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

Sources & evidence

ORD record
ord-69f120ac04c54e59b1b2db426843fe3e
Source dataset
uspto-grants-2012_01
Patent number
US08093388B2

Reaction notes

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