Sodium Thiosulfate → Methyl 3-(4-benzyloxyazepan-1-yl)sulfonyl-4-(2-hydroxyethyl)benzoate

HRID 713162Notes

Reaction equation

HRID 713162 reaction equation
[CH2:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][C:5]=1[S:14]([N:17]1[CH2:23][CH2:22][CH2:21][CH:20]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:19][CH2:18]1)(=[O:16])=[O:15])[CH:2]=C.[O-:32]S([O-])(=S)=O.[Na+].[Na+].[BH3-]C#N.[Na+]>C1COCC1.O.O=[Os](=O)(=O)=O>[CH2:25]([O:24][CH:20]1[CH2:21][CH2:22][CH2:23][N:17]([S:14]([C:5]2[CH:6]=[C:7]([CH:12]=[CH:13][C:4]=2[CH2:1][CH2:2][OH:32])[C:8]([O:10][CH3:11])=[O:9])(=[O:15])=[O:16])[CH2:18][CH2:19]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 3

HCID 24477Sodium ThiosulfateHCID 5003444Sodium cyanoborohydrideHCID 118222059Methyl 4-allyl-3-(4-benzyloxyazepan-1-yl)sulfonyl-benzoate

Product 1

HCID 118222043Methyl 3-(4-benzyloxyazepan-1-yl)sulfonyl-4-(2-hydroxyethyl)benzoateYield 53.88%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of methyl 4-allyl-3-(4-benzyloxyazepan-1-yl)sulfonyl-benzoate (630.00 mg, 1.42 mmol, 1.00 Eq) in THF (10 mL) and H2O (2 mL) were added OsO4 (36.10 mg, 142.00 umol, 0.10 Eq) and NaIO4 (607.45 mg, 2.84 mmol, 2.00 Eq) at 0° C. The mixture was stirred at 25° C. for 3 hr. TLC detected the reaction was complete, the mixture was poured into saturated Na2S2O3 solution, extracted with DCM, the combined organic layer was dried over anhydrous Na2SO4, concentrated, the residue was diluted in MeOH (10 mL), to the formed mixture was added NaBH3CN (88.86 mg, 1.41 mmol, 1.00 Eq). The mixture was stirred at 25° C. for 3 hr. TLC detected the reaction was complete, the reaction was quenched with water, extracted with EA, the combined organic layer was dried over anhydrous Na2SO4, concentrated, the residue was purified by chromatography (silica gel, eluting with PE:EA=3:1 to 1:1) to afford product methyl 3-(4-benzyloxyazepan-1-yl)sulfonyl-4-(2-hydroxyethyl)benzoate (340.00 mg, 759.71 umol, 53.88% yield). LCMS: 448 [M+1].

Workup

  1. extractionextracted with DCM
  2. dry with materialthe combined organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. additionthe residue was diluted in MeOH (10 mL), to the formed mixture
  5. stirringThe mixture was stirred at 25° C. for 3 hr
  6. customthe reaction was quenched with water
  7. extractionextracted with EA
  8. dry with materialthe combined organic layer was dried over anhydrous Na2SO4
  9. concentrationconcentrated
  10. customthe residue was purified by chromatography (silica gel, eluting with PE:EA=3:1 to 1:1)

Sources & evidence

ORD record
ord-5fd1e43d90e743a38fb4011ec1bb59bb
Source dataset
uspto-grants-2015_11
Patent number
US09181288B2

Reaction notes

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