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Boron tribromide → 5',7'-dimethyl-1'-(quinolin-2-ylmethyl)-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinolin]-6'-ol

HRID 2103089
Notes
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Reaction equation

HRID 2103089 reaction equation
C[O:2][C:3]1[C:4]([CH3:28])=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[N:9]([CH2:14][C:15]1[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]=1)[C:8]1([CH2:27][CH2:26][CH2:25]1)[CH2:7][CH2:6]2.B(Br)(Br)Br>C(Cl)Cl>[CH3:28][C:4]1[C:3]([OH:2])=[C:12]([CH3:13])[CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C:8]1([CH2:27][CH2:26][CH2:25]1)[N:9]2[CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 690595946'-methoxy-5',7'-dimethyl-1'-(quinolin-2-ylmethyl)-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinoline]

Product 1

HCID 578035295',7'-dimethyl-1'-(quinolin-2-ylmethyl)-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinolin]-6'-olYield 10.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

6′-Methoxy-5′,7′-dimethyl-1′-(quinolin-2-ylmethyl)-3′,4′-dihydro-1′H-spiro[cyclobutane-1,2′-quinoline] (250 mg) was dissolved in CH2Cl2 (10 mL). At 0° C., 2.5 mL of BBr3 (2 mL, 1M solution in CH2Cl2) was added to the flask. The mixture was stirred at 0° C. for 20 minutes and then at room temperature for 30 minutes. After removing the solvent and BBr3, the reaction was quenched by adding into it water. The aqueous solution was then extracted with ethyl acetate (3×20 mL). The organic layer was combined, dried over Na2SO4 and evaporated. The residue was purified by column chromatography (silicagel, 12% ethyl acetate/hexane), giving 5′,7′-dimethyl-1′-(quinolin-2-ylmethyl)-3′,4′-dihydro-1′H-spiro[cyclobutane-1,2′-quinolin]-6′-ol as a dark yellow solid (26 mg). 1H-NMR (300 MHz, CD3OD) δ=8.10 (m, 2H); 7.72-7.92 (m, 2H); 7.74 (m, 2H); 6.00 (s, 1H); 4.83 (s, 2H); 2.76 (s, 6H); 2.32 (m, 2H); 2.07 (s, 5H); 2.00 (s, 3H); 1.94 (m, 2H); 1.72 (m, 2H) ppm. MS: (m/z)=359 (100, M+H+)

Workup

  1. waitat room temperature for 30 minutes
  2. customAfter removing the solvent and BBr3
  3. customthe reaction was quenched
  4. additionby adding into it water
  5. extractionThe aqueous solution was then extracted with ethyl acetate (3×20 mL)
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue was purified by column chromatography (silicagel, 12% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-324d50014f7149eab7a4d8b4d63425d9
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576094B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes