Acetic Acid → 6'-methoxy-5',7'-dimethyl-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinoline]

HRID 2103083Notes

Reaction equation

HRID 2103083 reaction equation
[BH4-].[Na+].FC(F)(F)C(O)=O.C(O)(=O)C.[CH3:14][O:15][C:16]1[C:17]([CH3:31])=[C:18]2[C:23](=[CH:24][C:25]=1[CH3:26])[NH:22][C:21]1([CH2:29][CH2:28][CH2:27]1)[CH2:20][CH:19]2O>C1COCC1>[CH3:14][O:15][C:16]1[C:17]([CH3:31])=[C:18]2[C:23](=[CH:24][C:25]=1[CH3:26])[NH:22][C:21]1([CH2:27][CH2:28][CH2:29]1)[CH2:20][CH2:19]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 4311764Sodium borohydrideHCID 690563486'-methoxy-5',7'-dimethyl-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinolin]-4'-ol

Product 1

HCID 578035566'-methoxy-5',7'-dimethyl-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinoline]

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of NaBH4 (1 g) added in portions to a solution of cooled trifluoroacetic acid and acetic acid (30 mL, v/v: 1/1), was added 6′-methoxy-5′,7′-dimethyl-3′,4′-dihydro-1′H-spiro[cyclobutane-1,2′-quinolin]-4′-ol in 10 mL THF. After 30 minutes, the reaction mixture was quenched with water and extracted with ethyl acetate (3×20 mL). The organic layer was dried with Na2SO4, evaporated, and purified by column chromatography (1-2% methanol in CH2Cl2), to give 6′-methoxy-5′,7′-dimethyl-3′,4′-dihydro-1′H-spiro[cyclobutane-1,2′-quinoline] as a brown oil (500 mg).

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. dry with materialThe organic layer was dried with Na2SO4
  4. customevaporated
  5. custompurified by column chromatography (1-2% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-3cef2b3801844be99c89c3845cc9d404
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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