Cyano-borohydride → 4-((4-Fluoro-1-(oxetan-3-yl)piperidin-4-yl)methoxy)-3-nitrobenzenesulfonamide

HRID 1043222Notes

Reaction equation

HRID 1043222 reaction equation
[F:1][C:2]1([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][C:11]=2[N+:20]([O-:22])=[O:21])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[O:23]1[CH2:26][C:25](=O)[CH2:24]1.C([BH3-])#N>O1CCCC1.C(O)(=O)C>[F:1][C:2]1([CH2:8][O:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][C:11]=2[N+:20]([O-:22])=[O:21])[CH2:7][CH2:6][N:5]([CH:25]2[CH2:26][O:23][CH2:24]2)[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 498716Cyano-borohydrideHCID 150242543-OxetanoneHCID 671265024((4-Fluoropiperidin-4-yl)methoxy)-3-nitrobenzenesulfonamide

Product 1

HCID 671271554-((4-Fluoro-1-(oxetan-3-yl)piperidin-4-yl)methoxy)-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 341C (72 mg) in tetrahydrofuran (1.5 mL) and acetic acid (0.5 mL) was added oxetan-3-one (14 mg) and MP-cyanoborohydride (2.38 mmol/g, 162 mg). The mixture was stirred at room temperature overnight. The reaction was then filtered and the filtrate was concentrated under vacuum. The residue was slurried in ether and the product was collected by filtration.

Workup

  1. filtrationThe reaction was then filtered
  2. concentrationthe filtrate was concentrated under vacuum
  3. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-ed0df36af5d547f7b09908022f217309
Source dataset
uspto-grants-2013_10
Patent number
US08557983B2

Reaction notes

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