Hexane → HCID 11499733, compound

HRID 2103073Notes

Reaction equation

HRID 2103073 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15]C)=[C:10]([CH3:14])[C:11]=2[CH3:13])[CH2:6][C:5]2([CH2:19][CH2:18][CH2:17]2)[CH2:4]1)[CH3:2].B(Br)(Br)Br.CCOC(C)=O.CCCCCC>C(Cl)(Cl)Cl>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([OH:15])=[C:10]([CH3:14])[C:11]=2[CH3:13])[CH2:6][C:5]2([CH2:17][CH2:18][CH2:19]2)[CH2:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 25134Boron tribromideHCID 69053315HCID 69053315, compound

Product 1

HCID 11499733HCID 11499733, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1′-ethyl-6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline] (100 mg) in 2 mL chloroform cooled in ice bath (10° C.) was added BBr3 (2 mL, 1 M). After 4 hours, ice was added to quench the reaction. After separation of the two layers, dichloromethane was used to extract the aqueous phase. The combined organic phases were then washed with brine, dried and evaporated to give a crude oil which was then passed through a column (EtOAc: Hexane; 2-16%) to give 1′-ethyl-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinolin]-6′-ol (35.9 mg). 1H-NMR (300 MHz, CDCl3): δ=6.37 (s, 1H), 3.04 (s, 2H), 2.95-2.65 (q, 2H), 2.74 (s, 2H), 2.12 (s, 3H), 2.1 (s, 3H), 2.05-1.85 (m, 4H), 1.84-1.64 (m, 2H), 1.3-1.1 (t, 3H) ppm. 13C-NMR (75 MHz, CDCl3) δ=152.88, 143.52, 133.97, 130.4, 126.13, 116.74, 62.54, 55.07, 44.81, 42.13, 36.29, 19.77, 19.31, 16.6, and 15.79 ppm. MS: (m/z): 246.2 (M+H+)

Workup

  1. additionice was added
  2. customto quench
  3. customthe reaction
  4. customAfter separation of the two layers, dichloromethane
  5. extractionto extract the aqueous phase
  6. washThe combined organic phases were then washed with brine
  7. customdried
  8. customevaporated
  9. customto give a crude oil which

Sources & evidence

ORD record
ord-c96f721703824d87beb868f05c1b56e4
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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