Boron tribromide → HCID 11543630, compound

HRID 2235260Notes

Reaction equation

HRID 2235260 reaction equation
B(Br)(Br)Br.[CH:5]1([N:11]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[O:23]C)[C:12]2=[O:25])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.C(=O)(O)[O-].[Na+]>ClCCl>[CH:5]1([N:11]2[CH2:15][CH2:14][CH:13]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[OH:23])[C:12]2=[O:25])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 11716195HCID 11716195, compound

Product 1

HCID 11543630HCID 11543630, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add boron tribromide (0.21 mL, 2.2 mmol) to a solution of 1-cyclohexyl-3-(2-methoxy-benzyl)-pyrrolidin-2-one (210 mg, 0.73 mmol) in dichloromethane (5 mL). Stir 20 minutes. Pour mixture onto a mixture of ice and saturated sodium bicarbonate. Stir 5 minutes. Wash the organic layer with water, brine, dry, concentrate, and purify the residue on a Biotage cartridge, eluting with 4:1 hexanes:ethyl acetate to afford the title compound (115 mg): MS (APCI-pos mode) m/z (rel intensity) 274 (100).

Workup

  1. additionPour mixture
  2. stirringStir 5 minutes
  3. washWash the organic layer with water, brine
  4. customdry
  5. concentrationconcentrate
  6. custompurify the residue on a Biotage cartridge
  7. washeluting with 4:1 hexanes

Sources & evidence

ORD record
ord-19b1df534f5c414f805c3bef53a1d9d4
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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