Water → HCID 58494558, compound

HRID 1913169Notes

Reaction equation

HRID 1913169 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:19][CH:18]([C:20](OC)=[O:21])[CH2:17]2)(=[O:15])=[O:14])=[CH:9][CH:8]=1.[BH4-].[Na+].O.[OH-].[Na+]>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:8]=[CH:9][C:10]([S:13]([N:16]2[CH2:19][CH:18]([CH2:20][OH:21])[CH2:17]2)(=[O:14])=[O:15])=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 58494544HCID 58494544, compound

Product 1

HCID 58494558HCID 58494558, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 1-{[4-(pyridin-2-yl)phenyl]sulfonyl}azetidine-3-carboxylate (0.33 g, 0.99 mmol) in anhydrous methanol (20 mL) is added sodium borohydride (0.25 g, 6.58 mmol) portionwise. After 30 mins water (40 mL) is added followed by 5N aqueous NaOH. The aqueous layer is extracted with DCM. The organic layer is dried over Na2SO4, filtered and concentrated under reduced pressure to give 0.22 g (72%) of (1-{[4-(pyridin-2-yl)phenyl]sulfonyl}azetidin-3-yl)methanol. m/z=305 [M++H].

Workup

  1. extractionThe aqueous layer is extracted with DCM
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f505c6528cfb4d2aa97f0deed5a3e48b
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

Loading…