2-Bromopropane → HCID 86689025, compound

HRID 40524Notes

Reaction equation

HRID 40524 reaction equation
[OH:1][C:2]1[CH:24]=[CH:23][C:5]([O:6][CH:7]2[CH2:10][N:9]([C:11]3[CH:16]=[CH:15][C:14]([C@@H:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:13][CH:12]=3)[CH2:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:32]([CH3:34])[CH3:33]>CN(C=O)C>[CH:32]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]2[CH2:8][N:9]([C:11]3[CH:16]=[CH:15][C:14]([C@@H:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:13][CH:12]=3)[CH2:10]2)=[CH:23][CH:24]=1)([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 86689006(S)-N-(1-{4-[3-(4-Hydroxy-phenoxy)-azetidin-1-yl]-phenyl}-ethyl)-acetamide

Product 1

HCID 86689025HCID 86689025, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To 0.050 g (0.15 mmol) (S)—N-(1-{4-[3-(4-hydroxy-phenoxy)-azetidin-1-yl]-phenyl}-ethyl)-acetamide (VI.1) in 1.0 mL DMF are added 0.053 g (0.38 mmol) potassium carbonate and 17.2 μL (0.18 mmol) 2-bromopropane. The mixture is stirred for 12 h at 80° C. After cooling the mixture is directly purified by HPLC (XBridge, MeOH/water (+0.3% NH4OH)) to yield the desired product.

Workup

  1. temperatureAfter cooling the mixture
  2. customis directly purified by HPLC (XBridge, MeOH/water (+0.3% NH4OH))

Sources & evidence

ORD record
ord-47bd37b0818c4e3fa22644a3714bc66f
Source dataset
uspto-grants-2013_09
Patent number
US08530461B2

Reaction notes

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