6-Methoxy-alpha-tetralone → HCID 18434415, compound

HRID 1859084Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[N:6][CH:7]=1.[Li]CCCC.[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29](=[O:33])[CH2:28][CH2:27][CH2:26]2.C([O-])(O)=O.[Na+]>C1COCC1>[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[C:29]([C:2]1[CH:7]=[N:6][C:5]([O:8][CH2:9][CH2:10][N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)=[CH:4][CH:3]=1)([OH:33])[CH2:28][CH2:27][CH2:26]2

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 5-Bromo-2-(2-pyrrolidin-1-ylethoxy)pyridine (7.0 g, 26 mmol) in dry THF (50 mL) at -78° C. was added n-BuLi (2.5 M in hexanes, 12.4 mL, 31.0 mmol) dropwise. After 30 min, 6-methoxy-1-tetralone (4.55 g, 25.8 mmol) in dry THF was added. After stirring for 15 min at -78° C., the reaction was allowed to warm to room temperature. After 30 min, the reaction was poured into aq NaHCO3 (satd). The aqueous layer was extracted with EtOAc (2×). The combined organic solutions were dried (MgSO4), filtered, and concentrated. Flash chromatography (CHCl3 :MeOH, 95:5) provided the alcohol (4.23 g, 44%) as a white solid. 1H NMR (250 MHz, CDCl3): δ8.07 (d, J=2.5 Hz, 1H), 7.49 (dd, J=2.5, 8.7 Hz, 1H), 7.00 (d, J=8.5 Hz, 1H), 6.73 (m, 3H), 4.45 (t, J=5.7 Hz, 2H), 3.79 (s, 3H), 2.92 (t, J=5.7 Hz, 2H), 2.76 (m, 2H), 2.67 (m, 4H), 2.11 (s, 1H), 2.08 (m, 3H), 1.82 (m, 5H).

Workup

temperatureto warm to room temperature
waitAfter 30 min
extractionThe aqueous layer was extracted with EtOAc (2×)
dry with materialThe combined organic solutions were dried (MgSO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-15535e2f7ef2443abcedec6fb57b85b6
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06153622

Reaction notes

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