Water → (R)-1-(5-bromo-7-methylquinolin-6-yl)ethane-1,2-diol

HRID 2207043Notes

Reaction equation

CC[C@@H]1[C@@H]2C[C@H]([C@@H](OC3C4C(=CC=CC=4)C(O[C@@H](C4C=CN=C5C=4C=C(OC)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C([O:22]C)C=C4)N(CC2)C1.[OH2:59].[Br:60][C:61]1[C:70]([CH:71]=[CH2:72])=[C:69]([CH3:73])[CH:68]=[C:67]2[C:62]=1[CH:63]=[CH:64][CH:65]=[N:66]2>C(O)(C)(C)C.C(OCC)(=O)C>[Br:60][C:61]1[C:70]([C@@H:71]([OH:22])[CH2:72][OH:59])=[C:69]([CH3:73])[CH:68]=[C:67]2[C:62]=1[CH:63]=[CH:64][CH:65]=[N:66]2

Participants

Conditions

Temperature: 0 °C

Procedure

A biphasic mixture of AD-mix-β (1.2 g, excess) in tert-butanol (4.5 mL)/H2O (4.5 mL) was cooled to 0° C. and 5-bromo-7-methyl-6-vinylquinoline (210 mg, 0.85 mmol) was added. The reaction mixture was stirred for 2 days at 0° C. The mixture was diluted with ethyl acetate, washed with water and brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give (R)-1-(5-bromo-7-methylquinolin-6-yl)ethane-1,2-diol. 1H-NMR: 400 MHz, (CD3OD) δ 8.82 (d, J=4.4 Hz, 1H), 8.76 (d, J=8.8 Hz, 1H), 7.84 (s, 1H), 7.61-7.57 (m, 1H), 5.84 (dd, J=8.8, 4.8 Hz, 1H), 4.00 (dd, J=11.2, 8.8 Hz, 1H), 3.80 (dd, J=11.2, 4.4 Hz, 1H), 2.81 (s, 3 H).

Workup

washwashed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
custompurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-7e1e5e93ce894d87a3b175e386adda20
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376392B2

Reaction notes

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