Triethylamine → (5-Oxo-4-azaspiro[2.4]hept-7-yl)methyl methanesulfonate

HRID 595262Notes

Reaction equation

HRID 595262 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[OH:13][CH2:14][CH:15]1[C:19]2([CH2:21][CH2:20]2)[NH:18][C:17](=[O:22])[CH2:16]1>C(Cl)Cl.O>[CH3:1][S:2]([O:13][CH2:14][CH:15]1[C:19]2([CH2:21][CH2:20]2)[NH:18][C:17](=[O:22])[CH2:16]1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 916184147-(Hydroxymethyl)-4-azaspiro[2.4]heptan-5-one

Product 1

HCID 118216480(5-Oxo-4-azaspiro[2.4]hept-7-yl)methyl methanesulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.40 g, 1.0 mmol) and triethylamine (0.22 mL, 1.6 mmol) were added to a solution of 7-(hydroxymethyl)-4-azaspiro[2.4]heptan-5-one (0.11 g, 0.78 mmol) in DCM (4 mL) at 0° C. The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (10 mL×3). The organic layers were combined and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by silica gel chromatography (neat ethyl acetate, Rf=0.6) to afford (5-oxo-4-azaspiro[2.4]hept-7-yl)methyl methanesulfonate. 1H NMR (400 MHz, CDCl3) δ 5.87 (br s, 1H), 4.35-4.01 (m, 2H), 2.95 (s, 3H), 2.87-2.54 (m, 2H), 2.41-2.35 (m, 1H), 1.05-0.72 (m, 4H).

Workup

  1. extractionextracted with ethyl acetate (10 mL×3)
  2. concentrationconcentrated under reduced pressure
  3. customto afford the crude product residue
  4. customThe crude product residue was purified by silica gel chromatography (neat ethyl acetate, Rf=0.6)

Sources & evidence

ORD record
ord-52e48be9ce864b2c810fefda3ec56414
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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