Sodium borohydride → 6'-methoxy-5',7'-dimethyl-3',4'-dihydro-1'H-spiro[cyclobutane-1,2'-quinolin]-4'-ol

HRID 2103082Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]([CH3:18])=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[NH:9][C:8]1([CH2:16][CH2:15][CH2:14]1)[CH2:7][C:6]2=[O:17].[BH4-].[Na+]>CO.C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([CH3:18])=[C:5]2[C:10](=[CH:11][C:12]=1[CH3:13])[NH:9][C:8]1([CH2:14][CH2:15][CH2:16]1)[CH2:7][CH:6]2[OH:17]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 6′-methoxy-5′,7′-dimethyl-1′H-spiro[cyclobutane-1,2′-quinolin]-4′(3′H)-one (1 g) in a mixture of 35 mL methanol and 15 mL CH2Cl2, was added NaBH4 (2 g) slowly at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes and then at room temperature for three days. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was dried with Na2SO4 and evaporated, to yield 6′-methoxy-5′,7′-dimethyl-3′,4′-dihydro-1′H-spiro[cyclobutane-1,2′-quinolin]-4′-ol was used in the next step without further purification.

Workup

waitat room temperature for three days
customThe reaction mixture was quenched with water
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried with Na2SO4
customevaporated

Sources & evidence

ORD record: ord-c0fbd68fd053456da0c07c85ab9d59d7
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576094B2

Reaction notes

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