Acetic Acid → HCID 57803505, compound

HRID 2103072Notes

Reaction equation

HRID 2103072 reaction equation
[BH4-].[Na+].FC(F)(F)C(O)=O.C(O)(=O)C.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[C:24]([CH3:27])[C:25]=1[CH3:26])[NH:22][CH2:21][C:20]1([CH2:30][CH2:29][CH2:28]1)[CH:19]2O>C1COCC1>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[C:24]([CH3:27])[C:25]=1[CH3:26])[NH:22][CH2:21][C:20]1([CH2:28][CH2:29][CH2:30]1)[CH2:19]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 690602236'-methoxy-7',8'-dimethyl-2',4'-dihydro-1'H-spiro[cyclobutane-1,3'-quinolin]-4'-ol

Product 1

HCID 57803505HCID 57803505, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold solution of 6′-methoxy-7′,8′-dimethyl-1′H-spiro[cyclobutane-1,3′-quinolin]-4′(2′H)-one (2 g) in a mixture of 13 mL of THF and 5 mL of CH3OH cooled in ice bath, was added NaBH4 (2.4 g). After 2 hours, the mixture was quenched with ice, evaporated to dryness to give 6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinolin]-4′-ol as a crude mixture (11 g). NaBH4 (3 g) was added in portions to a mixture of trifluoroacetic acid and acetic acid (25 mL, v/v:1/1) cooled in ice bath, and to this mixture was added the above obtained mixture of 6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinolin]-4′-ol dissolved in 10 mL of THF. After 15 min, the mixture was quenched with ice, extracted with dichloromethane, and washed with brine. The organic phase was then washed with NaOH (2 M) and brine, dried, evaporated to dryness and passed through a silica column (Hexane: EtOAc; 10:1) to give 6′-methoxy-7′,8′-dimethyl-2′,4′-dihydro-1′H-spiro[cyclobutane-1,3′-quinoline] (1.3 g) as a liquid with slightly yellow color. 1H-NMR (300 MHz, CDCl3) δ=6.44071 (s, 1H), 3.74 (s, 3H), 3.59-3.24 (s, 1H), 3.18 (s, 2H), 2.75 (s, 2H), 2.13 (s, 3H), 2.03 (s, 3H), 2.01-1.73 (m, 6H) ppm. 13C-NMR (75 MHz, CDCl3) δ=149.88, 136.21, 123.51, 131.91, 118.09, 110.83, 56.51, 51.91, 40.82, 36.09, 30.84, 15.25, 13.07, and 12.03 ppm.

Workup

  1. temperaturecooled in ice bath
  2. additionto this mixture was added
  3. customthe mixture was quenched with ice
  4. extractionextracted with dichloromethane
  5. washwashed with brine
  6. washThe organic phase was then washed with NaOH (2 M) and brine
  7. customdried
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-a94a97d3b0404350a3fe8074bf78e929
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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