Methanesulfonyl chloride → tert-Butyl 2-((methylsulfonyl)oxy)-7-azaspiro[3.5]nonane-7-carboxylate

HRID 890030Notes

Reaction equation

HRID 890030 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:11]2([CH2:14][CH:13]([OH:15])[CH2:12]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>O1CCCC1.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([CH2:12][CH:13]([O:15][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:14]2)[CH2:16][CH2:17]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 9834677Tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate

Product 1

HCID 22248489tert-Butyl 2-((methylsulfonyl)oxy)-7-azaspiro[3.5]nonane-7-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

After dissolving 106 mg of 7-(tert-butoxycarbonyl)-2-hydroxy-7-azaspiro[3.5]nonane in 10 ml of tetrahydrofuran, 0.04 ml of methanesulfonyl chloride and 0.07 ml of triethylamine were added and the mixture was stirred overnight at room temperature. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. After adding water to the residue, extraction was performed with ethyl acetate. The organic layer was washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (148 mg, 100% yield).

Workup

  1. additionwere added
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionAfter adding water
  5. extractionto the residue, extraction
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0961fd66930f4fb799f84d3e9b59c80c
Source dataset
uspto-grants-2006_02
Patent number
US06995144B2

Reaction notes

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