Sodium Hydroxide → 5'-(3,7-dimethylocta-2,6-dienyl)-1'-(4-methoxyphenyl)-7',8'-dimethyl-2',4'-dihydro-1'H-spiro[cyclobutane-1,3'-quinolin]-6'ol

HRID 2103090Notes

Reaction equation

HRID 2103090 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:18]3[C:13](=[CH:14][C:15]([OH:21])=[C:16]([CH3:20])[C:17]=3[CH3:19])[CH2:12][C:11]3([CH2:24][CH2:23][CH2:22]3)[CH2:10]2)=[CH:5][CH:4]=1.[OH-].[Na+].[CH2:27](Br)/[CH:28]=[C:29](/[CH2:31][CH2:32][CH:33]=[C:34]([CH3:36])[CH3:35])\[CH3:30].[NH4+].[Cl-]>CC(O)(C)C>[CH3:30][C:29]([CH2:31][CH2:32][CH:33]=[C:34]([CH3:36])[CH3:35])=[CH:28][CH2:27][C:14]1[C:15]([OH:21])=[C:16]([CH3:20])[C:17]([CH3:19])=[C:18]2[C:13]=1[CH2:12][C:11]1([CH2:22][CH2:23][CH2:24]1)[CH2:10][N:9]2[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 53658672,6-Octadiene, 1-bromo-3,7-dimethyl-, (2E)-HCID 690555481'-(4-methoxyphenyl)-7',8'-dimethyl-1',4'-dihydro-2'H-spiro[cyclobutane-1,3'-quinolin]-6'-ol

Product 1

HCID 690546255'-(3,7-dimethylocta-2,6-dienyl)-1'-(4-methoxyphenyl)-7',8'-dimethyl-2',4'-dihydro-1'H-spiro[cyclobutane-1,3'-quinolin]-6'ol

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of 1′-(4-methoxyphenyl)-7′,8′-dimethyl-1′,4′-dihydro-2′H-spiro[cyclobutane-1,3′-quinolin]-6′-ol (112 mg) in 3.2 mL t-BuOH was added NaOH (224 μL) and geranyl bromide (133 μL). After 20 minutes, saturated NH4Cl was added and the mixture was extracted with dichloromethane. The organic phase was then washed with brine, dried and evaporated. The residue was passed through a column (Hexane:EtOAc=10:1.2-10:2) to give 5′-(3,7-dimethylocta-2,6-dienyl)-1′-(4-methoxyphenyl)-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinolin]-6′ol (14.7 mg) as a semi white solid. 1H-NMR (300 MHz, CDCl3) δ=6.79-6.62 (m, 4H); 5.26-5.13 (m, 1H); 5.13-5.01 (m, 1H); 4.93 (s, 1H); 3.76 (s, 3H); 3.61 (s, 2H); 2.79 (s, 2H); 2.17-2.02 (m, 7H); 1.82-1.28 (m, 18H). 13C-NMR (75 MHz, CDCl3) δ=152.74, 148.42, 146.18, 138.01, 135.33, 131.98, 129.67, 126.73, 123.86, 122.39, 122.12, 121.95, 119.93, 113.99, 76.63, 61.49, 55.51, 40.16, 39.75, 38.33, 32.89, 26.46, 25.75, 25.53, 17.77, 16.27, 15.76, 15.61, 12.39 ppm.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic phase was then washed with brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-62d7dd9c923f4757bd42b9ff770dad6f
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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