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

HRID 1244453Notes

Reaction equation

HRID 1244453 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-22a77e7ee05e488b9dcdc93c7dfb2a68
Source dataset
uspto-grants-2006_10
Patent number
US07122558B2

Reaction notes

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