Isobutylene → 3-(3-Chloro-6-hydroxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-one

HRID 1173832Notes

Reaction equation

HRID 1173832 reaction equation
[Cl:1][C:2]1[C:3]2[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][C:4]=2[S:5][C:6]=1[CH2:7][CH:8]1[CH2:12][CH2:11][N:10]([CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:9]1=[O:19].CC(=C)C.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[C:3]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][C:4]=2[S:5][C:6]=1[CH2:7][CH:8]1[CH2:12][CH2:11][N:10]([CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]2)[C:9]1=[O:19]

Participants

5

Reactant 3

HCID 8255IsobutyleneHCID 25134Boron tribromideHCID 114945963-(3-Chloro-6-methoxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexylpyrrolidin-2-one

Product 1

HCID 117103063-(3-Chloro-6-hydroxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexyl-pyrrolidin-2-oneYield 103.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3-(3-chloro-6-methoxy-benzo[b]thiophen-2-ylmethyl)-1-cyclohexylpyrrolidin-2-one (1.122 g, 2.97 mmol) and 2-methyl-2 propene (0.5 mL) in dichloromethane (30 mL) and cool to 0° C. Slowly add boron tribromide (2.23 g, 8.91 mmol) and warm to room temperature. Stir for 1 hour and quench with ice. Extract with dichloromethane, dry with sodium sulfate, filter, and concentrate to give the title compound (1.121 g, 99%) as a light brown solid: Mass spectrum (apci) m/z=364.2 (M+H).

Workup

  1. customquench with ice
  2. extractionExtract with dichloromethane
  3. dry with materialdry with sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-352c25ab1ae84a94bd714e14ad29e5ff
Source dataset
uspto-grants-2010_11
Patent number
US07834194B2

Reaction notes

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