Hydrochloric Acid → 7',8'-dimethyl-2',3'-dihydro-1'H-spiro[cyclobutane-1,4'-quinolin]-6'-ol

HRID 2103086Notes

Reaction equation

HRID 2103086 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:13])[C:11]=1[CH3:12])[NH:8][C:7](=O)[CH2:6][C:5]12[CH2:17][CH2:16][CH2:15]1.B.C1COCC1.Cl>C1COCC1>[CH3:12][C:11]1[C:10]([CH3:13])=[C:9]2[C:4]([C:5]3([CH2:15][CH2:16][CH2:17]3)[CH2:6][CH2:7][NH:8]2)=[CH:3][C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 690541776'-hydroxy-7',8'-dimethyl-1'H-spiro[cyclobutane-1,4'-quinolin]-2'(3'H)-one

Product 1

HCID 578035137',8'-dimethyl-2',3'-dihydro-1'H-spiro[cyclobutane-1,4'-quinolin]-6'-olYield 16.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6′-hydroxy-7′,8′-dimethyl-1′H-spiro[cyclobutane-1,4′-quinolin]-2′(3′H)-one (4.6 g) in THF was added to BH3-THF (45 mL) at 0° C. The mixture was stirred at room temperature for 20 minutes and allowed to reflux overnight. The mixture was cooled down and at 0° C., 3 N HCl was added to quench the excess BH3. The solvent was removed by evaporation. The solid present was collected by filtration and washed with hexane (×3), giving 7′,8′-dimethyl-2′,3′-dihydro-1′H-spiro[cyclobutane-1,4′-quinolin]-6′-ol (700 mg) as a light yellow solid. 1H-NMR (300 MHz, CDCl3) δ=6.54 (s, 2H); 4.21 (t, J=6 Hz, 2H); 2.15 (m, 5H); 2.02 (m, 8H); 2.19 (m, 8H); 1.94 (t, J=6 Hz, 2H) ppm. MS: (m/z)=218 (100, M+H+).

Workup

  1. temperatureto reflux overnight
  2. temperatureThe mixture was cooled down and at 0° C.
  3. customto quench the excess BH3
  4. customThe solvent was removed by evaporation
  5. filtrationThe solid present was collected by filtration
  6. washwashed with hexane (×3)

Sources & evidence

ORD record
ord-dd705221b32343d785de0a42d721c566
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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