Triethylamine → 3-(Boc-amino)-1-methanesulfonylpyrrolidine

HRID 2191566Notes

Reaction equation

HRID 2191566 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:13][CH2:12][N:11]([S:22]([CH3:21])(=[O:24])=[O:23])[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamate

Product 1

HCID 587241113-(Boc-amino)-1-methanesulfonylpyrrolidineYield 127%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 15 mL round-bottomed flask, 3-(tert-butoxycarbonylamino)pyrrolidine (0.50 g, 2.68 mmol) was dissolved in CH2Cl2 (5 mL). Triethylamine (0.45 mL, 3.22 mmol) was added and the reaction mixture was cooled to 0° C. Methanesulfonyl chloride (0.25 mL, 3.22 mmol) was added dropwise and the reaction mixture was slowly warmed to room temperature and stirred overnight. The reaction was diluted with CH2Cl2 (20 mL) and quenched with 1.0 M aqueous HCl (5 mL). The aqueous layer was extracted with CH2Cl2 then the combined organics were dried over Na2SO4, filtered and concentrated to afford 0.90 g of (1-methanesulfonyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester as a light brown solid which was used without further purification.

Workup

  1. temperaturethe reaction mixture was slowly warmed to room temperature
  2. customquenched with 1.0 M aqueous HCl (5 mL)
  3. extractionThe aqueous layer was extracted with CH2Cl2
  4. dry with materialthe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7f48281271484fe093e619007acf2f2b
Source dataset
uspto-grants-2012_12
Patent number
US08329699B2

Reaction notes

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