Pyrrolidine → HCID 70982893, compound

HRID 1506751Notes

Reaction equation

HRID 1506751 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])(=O)=O.[NH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>C1COCC1>[N:21]1([CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11](=[O:12])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 11141145N-(benzyloxycarbonyl)-4-(mesyloxy)butylamine

Product 1

HCID 70982893HCID 70982893, compoundYield 65.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a pressure vessel was added 4-(benzyloxycarbonylamino)butyl methanesulfonate (330 mg, 1.10 mmol) and pyrrolidine (234 mg, 3.3 mmol) in THF. The reaction was heated to 100° C., stirred overnight, cooled to 20-25° C., and concentrated. The crude concentrate was purified by Biotage column chromatography to give benzyl 4-(pyrrolidin-1-yl)butylcarbamate (200 mg).

Workup

  1. temperaturecooled to 20-25° C.
  2. concentrationconcentrated
  3. concentrationThe crude concentrate
  4. customwas purified by Biotage column chromatography

Sources & evidence

ORD record
ord-a6e1e4e716004fd9bae0b55d6f38032d
Source dataset
uspto-grants-2015_12
Patent number
US09221760B2

Reaction notes

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