Sodium Bicarbonate → HCID 59331266, compound

HRID 1881950Notes

Reaction equation

HRID 1881950 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[N:22]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:23]([C:26]4[CH:31]=[CH:30][C:29]([CH:32]=[O:33])=[CH:28][N:27]=4)=[CH:24][CH:25]=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.[BH4-].[Na+].C(=O)([O-])O.[Na+]>C(O)C>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([C:21]3[N:22]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[C:23]([C:26]4[CH:31]=[CH:30][C:29]([CH2:32][OH:33])=[CH:28][N:27]=4)=[CH:24][CH:25]=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

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 59331346HCID 59331346, compound

Product 1

HCID 59331266HCID 59331266, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of tert-butyl 2-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-5-(5-formylpyridin-2-yl)-1H-pyrrole-1-carboxylate (3 g) in ethanol (10 mL) was added sodium borohydride (221 mg), and the mixture was stirred at room temperature for 10 min. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, 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, and the title compound (3 g, yield 100%) was obtained as a pale-yellow amorphous solid from a fraction eluted with hexane-ethyl acetate (1:1, volume ratio). MS: 567 (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-1312d02be7a74de584007a5cb60b6aa3
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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