HCID 59299525, compound → HCID 178515522, compound

HRID 2235283Notes

Reaction equation

HRID 2235283 reaction equation
[Cl:1][C:2]1[CH:20]=[C:19]([C:21]2[C:22]([O:27]C)=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:18]=[CH:17][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:6]1=[O:16]>ClCCl>[Cl:1][C:2]1[CH:20]=[C:19]([C:21]2[C:22]([OH:27])=[N:23][CH:24]=[CH:25][CH:26]=2)[CH:18]=[CH:17][C:3]=1[CH2:4][CH:5]1[CH2:9][CH2:8][N:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[C:6]1=[O:16]

Participants

3

Reactant 1

HCID 59299525HCID 59299525, compound

Product 1

HCID 178515522HCID 178515522, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Place 3-(2-chloro-4-(2-methoxypyridin-3-yl)benzyl)-1-cyclohexylpyrrolidin-2-one (Example 105) (120 mg, 0.3 mmol) in dichloromethane (10 mL) and cool to 0° C. Add borontribromide (226 mg, 0.9 mmol) and stir of 16 hours. Add water and extract with dichloromethane. Dry over sodium sulfate, filter, and concentrate. Purify by silica gel (10% methanol in dichloromethane) to yield 65 mg (56%) of the title compound: Mass spectrum (apci) m/z=385.2 (M+H).

Workup

  1. additionAdd borontribromide (226 mg, 0.9 mmol)
  2. extractionAdd water and extract with dichloromethane
  3. dry with materialDry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by silica gel (10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-508c89a3fc184becadb9734c5aa70084
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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