Methanol → 2-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethanol

HRID 1882114Notes

Reaction equation

HRID 1882114 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[N:31]=[CH:30][C:29]([CH2:32][C:33](OC)=[O:34])=[CH:28][CH: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.O1CCCC1.CO.[BH4-].[Li+]>O>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([C:21]3[NH:25][C:24]([C:26]4[N:31]=[CH:30][C:29]([CH2:32][CH2:33][OH:34])=[CH:28][CH:27]=4)=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 59331493methyl [6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]acetate

Product 1

HCID 593313752-[6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of methyl [6-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)pyridin-3-yl]acetate (400 mg), tetrahydrofuran (10 mL) and methanol (2 mL) was added lithium borohydride (85 mg) at room temperature, and the mixture was stirred at room temperature for 3 hr. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to give the title compound as a crude product from a fraction eluted with hexane-ethyl acetate-methanol (1:4:0-0:95:5, volume ratio), the crude product was subjected to preparative HPLC to give the title compound (150 mg, yield 39%) as a pale-yellow amorphous solid. MS: 481 (MH+).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-3b688f6f448742668ac5c7e9d657c402
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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