Methanesulfonic Acid → (R)-3-Aminopentanenitrile Methanesulfonic Acid Salt

HRID 2120330Notes

Reaction equation

HRID 2120330 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].C(OC(=O)[NH:12][CH:13]([CH2:16][C:17]#[N:18])[CH2:14][CH3:15])(C)(C)C>O1CCCC1>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[NH2:12][C@H:13]([CH2:14][CH3:15])[CH2:16][C:17]#[N:18]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 21629520tert-butyl N-(1-cyanobutan-2-yl)carbamate

Product 1

HCID 57350099(R)-3-Aminopentanenitrile Methanesulfonic Acid Salt

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Methane sulfonic acid (71 g) was added to a solution of (1-cyanomethyl-propyl)-carbamic acid tert-butyl ester in tetrahydrofuran (530 mL). The reaction mixture was heated to 40° C. for approximately 30 minutes. The temperature was raised to 45° C. and stirred for approximately one hour. The temperature was raised again to 65° C. and the reaction mixture was stirred for five hours. The mixture was allowed to cool to ambient temperature. The resulting solids were isolated by filtration to afford the title compound (41.53 g).

Workup

  1. temperatureThe temperature was raised to 45° C.
  2. temperatureThe temperature was raised again to 65° C.
  3. stirringthe reaction mixture was stirred for five hours
  4. temperatureto cool to ambient temperature
  5. customThe resulting solids were isolated by filtration

Sources & evidence

ORD record
ord-4050e2d968e6450ca602020bbad682f6
Source dataset
uspto-grants-2004_02
Patent number
US06689897B2

Reaction notes

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