tert-Butanol → (2s)-4-[5-(Benzyloxy)quinolin-6-yl]butane-1,2-diol

HRID 47958Notes

Reaction equation

HRID 47958 reaction equation
C(OC1C(CCC=C)=CC=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2)C1C=CC=CC=1.CC[C@H]1[C@H]2C[C@H]([C@H](OC3[C:56]4[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=4)[C:50]([O:57][C@H:58]([C:69]4[CH:78]=[CH:77]N=C5[C:70]=4[CH:71]=[C:72]([O:79]C)C=C5)[C@@H]4N5C[C@H](CC)[C@@H](CC5)C4)=NN=3)C3C=CN=C4C=3C=C(OC)C=C4)N(CC2)C1.[C:81]([OH:85])(C)(C)C>O>[CH2:50]([O:57][C:58]1[C:69]([CH2:70][CH2:71][C@H:72]([OH:79])[CH2:81][OH:85])=[CH:78][CH:77]=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2)[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 234318275-(Benzyloxy)-6-but-3-enylquinolineHCID 510036741-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine

Product 1

HCID 67550968(2s)-4-[5-(Benzyloxy)quinolin-6-yl]butane-1,2-diol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Addition of 5-(benzyloxy)-6-but-3-enylquinoline to a suspension of AD-mix-α in water:tert-butyl alcohol following the procedure described for Example 1, step 2 gives (2S)-4-[5-(benzyloxy)quinolin-6-yl]butane-1,2-diol.

Sources & evidence

ORD record
ord-50091c68ecd04f71b58065b5c393fb54
Source dataset
uspto-grants-2004_03
Patent number
US06700001B2

Reaction notes

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