Pyrrolidine → ((R)-1-methyl-3-oxo-3-pyrrolidin-1-yl-propyl)-carbamic acid tert-butyl ester

HRID 245986Notes

Reaction equation

HRID 245986 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:14])[CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2[CH:26]=[CH:27][CH:28]=[N:29][C:24]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1CCCC1>CN(C=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH3:14])[CH2:10][C:11](=[O:13])[N:29]1[CH2:28][CH2:27][CH2:26][CH2:24]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 2761507(R)-3-((tert-butoxycarbonyl)amino)butanoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 71280091((R)-1-methyl-3-oxo-3-pyrrolidin-1-yl-propyl)-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-3-tert-butoxycarbonylamino-butyric acid (150 mg, 0.74 mmol) and HATU (309 mg, 0.81 mmol) in DMF (2 mL) was added pyrrolidine (0.19 mL, 2.21 mmol). The resultant yellow reaction mixture was stirred at room temperature overnight then quenched with water and extracted with EtOAc (2×). The combined organics were washed with water (3×) and brine then dried over MgSO4 and concentrated to afford ((R)-1-methyl-3-oxo-3-pyrrolidin-1-yl-propyl)-carbamic acid tert-butyl ester as a colorless oil which was used without further purification.

Workup

  1. customthen quenched with water
  2. extractionextracted with EtOAc (2×)
  3. washThe combined organics were washed with water (3×) and brine
  4. dry with materialthen dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1c7ca478f1694f36946f8e189de697d9
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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