Acetone → 1'-(4-chlorophenyl)-6'-methoxy-5',7',8'-trimethyl-2',4'-dihydro-1'H-spiro[cyclobutane-1,3'-quinolin]-4'-ol

HRID 2103066Notes

Reaction equation

HRID 2103066 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17]3[C:12](=[C:13]([CH3:22])[C:14]([O:20][CH3:21])=[C:15]([CH3:19])[C:16]=3[CH3:18])[C:11](=[O:23])[C:10]3([CH2:26][CH2:25][CH2:24]3)[CH2:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+].CC(C)=O.CCOC(C)=O>C1COCC1.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:17]3[C:12](=[C:13]([CH3:22])[C:14]([O:20][CH3:21])=[C:15]([CH3:19])[C:16]=3[CH3:18])[CH:11]([OH:23])[C:10]3([CH2:24][CH2:25][CH2:26]3)[CH2:9]2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 180AcetoneHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 690567921'-(4-chlorophenyl)-6'-methoxy-5',7',8'-trimethyl-1'H-spiro[cyclobutane-1,3'-quinolin]-4'(2'H)-one

Product 1

HCID 690544051'-(4-chlorophenyl)-6'-methoxy-5',7',8'-trimethyl-2',4'-dihydro-1'H-spiro[cyclobutane-1,3'-quinolin]-4'-olYield 79.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1′-(4-chlorophenyl)-6′-methoxy-5′,7′,8′-trimethyl-1′H-spiro[cyclobutane-1,3′-quinolin]-4′(2′H)-one (80 mg) in THF (6 mL) and methanol (1.5 mL) cooled in ice bath, was added NaBH4 (81.7 mg). After 1.5 h, 5 mL acetone was added to the solution and the mixture was evaporated to yield a thick oil, which was taken up by EtOAc. The organic phase was then washed with brine, dried and evaporated to give 1′-(4-chlorophenyl)-6′-methoxy-5′,7′,8′-trimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinolin]-4′-ol (64.3 mg) 1H-NMR (300 MHz, CDCl3) δ=7.21-6.977 (d, 2H); 6.67 (br s, 2H); 4.745 (s, 1H); 3.949-3.753 (d, 1H); 3.687 (s, 3H); 3.629-3.54 (d, 1H); 2.426 (s, 3H); 2.312-2.174 (m, 1H); 2.147 (s, 3H); 1.967-1.737 (m, 3H); 1.705 (s, 3H); 1.672-1.489 (m, 2H) ppm.

Workup

  1. customthe mixture was evaporated
  2. customto yield a thick oil, which
  3. washThe organic phase was then washed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-6a94f150889f449996e33e87791d0161
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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