tert-Butanol → 1-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diol

HRID 1881969Notes

Reaction equation

HRID 1881969 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[CH:31]=[CH:30]C(C=C)=[CH:28][N:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[C:34]([OH:38])(C)([CH3:36])[CH3:35].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:60]C)C=C4)N(CC2)C1.S([O-])([O-])=O.[Na+].[Na+]>C(OC)(=O)C.O>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[N:27]=[CH:28][C:35]([CH:34]([OH:38])[CH2:36][OH:60])=[CH:30][CH:31]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 24437Sodium SulfiteHCID 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)phthalazineHCID 593314472-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-5-ethenylpyridine

Product 1

HCID 251070761-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethane-1,2-diolYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6584Methyl AcetateSolvent

Procedure

To a solution of 2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-5-ethenylpyridine (110 mg) in a mixed solvent of tert-butyl alcohol (1.5 mL) and water (1.5 mL) was added AD-mix-α (350 mg; Aldrich), and the mixture was stirred under ice-cooling for 4 hr. Sodium sulfite (30 mg) was added and the mixture was stirred for 30 min. The reaction mixture was diluted with methyl acetate, washed with water and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to preparative HPLC to give the title compound (47 mg, yield 40%) as a yellow amorphous solid. MS: 497 (MH+).

Workup

  1. temperaturecooling for 4 hr
  2. stirringthe mixture was stirred for 30 min
  3. washwashed with water and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d25bd9bfaa8f4a1785b13c3cef677368
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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