Dimethylacetamide → (1S,2S)-N,N-dimethyl-(6-fluoro-2-hydroxy-1-isopropyl-1, 2,3,4-tetrahydronaphthalen-2-yl)acetamide

HRID 2394995Notes

Reaction equation

C([N-]C(C)C)(C)C.[Li+].[CH3:9][N:10]([CH3:14])[C:11](=[O:13])[CH3:12].[F:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C@H:22]([CH:26]([CH3:28])[CH3:27])[C:21](=[O:29])[CH2:20][CH2:19]2>O1CCCC1>[CH3:9][N:10]([CH3:14])[C:11](=[O:13])[CH2:12][C@@:21]1([OH:29])[CH2:20][CH2:19][C:18]2[C:23](=[CH:24][CH:25]=[C:16]([F:15])[CH:17]=2)[C@@H:22]1[CH:26]([CH3:27])[CH3:28]

Participants

Conditions

Temperature: -55 °C

Procedure

Lithium diisopropylamide, 1.3 mL of 0.84 molar solution in tetrahydrofuran, was added to a solution of 0.11 mL N,N-dimethylacetamide in 1 mL tetrahydrofuran at -78° C. The mixture was stirred for fifteen minutes, then allowed to warm to -55° C. A solution of 220 mg (S)-6-fluoro-1-isopropyl-3,4-dihydro-1H-naphthalen-2-one in 1 mL tetrahydrofuran was added at that temperature, then allowed to warm to 0-5° C. with stirring, and stirred for 2.5 hours. The reaction mixture was quenched with 3 mL saturated aqueous ammonium chloride, and extracted three times with 3 mL portions of diethyl ether. The ether extracts were combined, dried with magnesium sulfate, and stripped to give 290 mg (1S,2S)-N,N-dimethyl-(6-fluoro-2-hydroxy-1-isopropyl-1, 2,3,4-tetrahydronaphthalen-2-yl)acetamide as a pale yellow oil.

Workup

temperatureto warm to 0-5° C.
stirringwith stirring
stirringstirred for 2.5 hours
customThe reaction mixture was quenched with 3 mL saturated aqueous ammonium chloride
extractionextracted three times with 3 mL portions of diethyl ether
dry with materialdried with magnesium sulfate

Sources & evidence

ORD record: ord-66454c71968945b1b20b913b022e9922
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05811556

Reaction notes

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