Methanesulfonyl chloride → 7-Methanesulfonyl-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester

HRID 1778465Notes

Reaction equation

HRID 1778465 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:16]2[CH2:17][NH:18][CH2:19][CH:12]1[CH2:13][O:14][CH2:15]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH:16]2[CH2:17][N:18]([S:30]([CH3:29])(=[O:32])=[O:31])[CH2:19][CH:12]1[CH2:13][O:14][CH2:15]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 673561213-Oxa-7,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester

Product 1

HCID 1176975127-Methanesulfonyl-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl esterYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound X) (100 mg, 0.33 mmol) in CH2Cl2 (5 mL) was added DIPEA (0.23 mL, 1.32 mmol) and methanesulfonyl chloride (57 mg, 0.49 mol). The reaction mixture was stirred at room temperature for 1 hour, and then quenched with sat. NH4Cl, then diluted with EtOAc (60 mL). The mixture was washed with sat. NH4Cl, sat. NaHCO3 and brine (20 mL) respectively. The organic layer was dried over Na2SO4. The solvent was removed under reduced pressure to give 7-methanesulfonyl-3-oxa-7,9-diaza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound Y) (105 mg, 95%) as yellowish oil. MS: calc'd (MH+) 341, measured (MH+) 341.

Workup

  1. customquenched with sat. NH4Cl
  2. additiondiluted with EtOAc (60 mL)
  3. washThe mixture was washed with sat. NH4Cl, sat. NaHCO3 and brine (20 mL) respectively
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-2a07fb3d4ba640d49c8cbec45b6fbd01
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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