HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 2207043
Notes
Print preview

Reaction equation

HRID 2207043 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 112172021,4-Bis(dihydroquinidine)phthalazineHCID 666306625-Bromo-7-methyl-6-vinylquinoline

Product 1

HCID 89676590(R)-1-(5-bromo-7-methylquinolin-6-yl)ethane-1,2-diol

Reagents, catalysts & solvents 2

HCID 6386tert-ButanolSolvent
HCID 8857
Ethyl Acetate
Solvent

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

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. 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

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes