Triethylamine → HCID 86761097, compound

HRID 2233259Notes

Reaction equation

HRID 2233259 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([N:15]1[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C(OCC)C>[CH3:21][S:22]([OH:24])(=[O:12])=[O:23].[C:8]([O:12][C:13]([N:15]1[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 86761097HCID 86761097, compoundYield 191.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Triethylamine (4.5 ml, 32.0 mmol) was added to a stirred solution of, N-(tert-butoxy-carbonyl)-3-hydroxypyrrolidine (2.00 g, 10.7 mmol) in diethyl ether (100 ml) and the reaction was cooled to 0° C. before addition of methanesulphonyl chloride (1.65 ml, 21.4 mmol) and stirring for 2 hours, warming from 0° C. to ambient temperature. The reaction was filtered, the filtrate was washed with 1.0 N hydrochloric acid (100 ml) and with brine (100 ml) before being dried over magnesium sulphate. Solvent evaporation in vacuo yielded N-(tert-butoxycarbonyl)-3-hydroxypyrrolidine methanesulphonate (2.9 g, 100% yield) as a colourless oil:

Workup

  1. temperaturewarming from 0° C. to ambient temperature
  2. filtrationThe reaction was filtered
  3. washthe filtrate was washed with 1.0 N hydrochloric acid (100 ml) and with brine (100 ml)
  4. dry with materialbefore being dried over magnesium sulphate
  5. customSolvent evaporation in vacuo

Sources & evidence

ORD record
ord-d6384683522e401cadb1a8953d93b1d3
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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