Benzene, (3-bromopropoxy)- → HCID 10301703, compound

HRID 1366717Notes

Reaction equation

HRID 1366717 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:21])[C:11]([OH:20])([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[CH2:12][CH:13]=[CH2:14])[CH2:2]2.[O:22]([CH2:29][CH2:30][CH2:31][Br:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(#N)C.C(Cl)(Cl)Cl>[Br-:32].[OH:20][C:11]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)([CH2:12][CH:13]=[CH2:14])[C:10]([O:9][C@@H:3]1[CH:4]2[CH2:5][CH2:6][N+:1]([CH2:31][CH2:30][CH2:29][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([CH2:8][CH2:7]2)[CH2:2]1)=[O:21]

Participants

5

Reactant 2

HCID 68522Benzene, (3-bromopropoxy)-HCID 66959055HCID 66959055, compound

Product 1

HCID 10301703HCID 10301703, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

250 mg (0.81 mmol) of 2-Hydroxy-2-thien-2-ylpent-4-enoic acid (3R)-1-azabicyclo[2.2.2]oct-3-yl ester, Intermediate I-3, were dissolved in 5 ml of acetonitrile and 7.5 ml of chloroform. To this solution were added 0.63 ml (4.1 mmol) of phenoxypropylbromide. After stirring for 48 h at room temperature under a N2 atmosphere, solvents were evaporated. Ether was added and the mixture stirred. The solid obtained was filtered and washed several times with ether. The yield was 0.3 g (71%) of the title compound as a mixture of diastereomers; mp: 157° C.

Workup

  1. customsolvents were evaporated
  2. additionEther was added
  3. stirringthe mixture stirred
  4. customThe solid obtained
  5. filtrationwas filtered
  6. washwashed several times with ether
  7. additionThe yield was 0.3 g (71%) of the title compound as a mixture of diastereomers

Sources & evidence

ORD record
ord-507bc509c8e54daebb641d328e893531
Source dataset
uspto-grants-2011_02
Patent number
US07893087B2

Reaction notes

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