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 1881969ノート

反応式

HRID 1881969 の反応式
[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

参加物

7

反応物 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

生成物 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-diol収率 40%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6584Methyl Acetate溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-d25bd9bfaa8f4a1785b13c3cef677368
出典データセット
uspto-grants-2012_11
特許番号
US08318746B2

反応ノート

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