Cyclobutylamine → (S)-2-Cyclobutylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

HRID 1970635Notes

Reaction equation

HRID 1970635 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]([OH:18])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:19]1[CH:24]=NC2N(O)N=[N:27][C:21]=2[CH:20]=1.CCN(C(C)C)C(C)C.C1(N)CCC1>CN(C=O)C.C(OCC)(=O)C.C(Cl)CCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16](=[O:18])[NH:27][CH:21]1[CH2:20][CH2:19][CH2:24]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 75645CyclobutylamineHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 232388N-(Carbobenzyloxy)-DL-proline

Product 1

HCID 66854900(S)-2-Cyclobutylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5.00 g pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester in 100 ml DMF were added 2.73 g HOAt, 3.85 g EDC, 6.9 ml DIPEA and 1.43 g cyclobutylamine. After 24 h the mixture was diluted with ethyl acetate and subsequently extracted with aqueous LiCl (4% w/w), 0.1 M HCl and saturated aqueous NaHCO3. The organic layer was dried over MgSO4 and the solvent was removed under reduced pressure to give the crude which was pure enough for the subsequent transformation. Yield: 9.00 g.

Workup

  1. extractionsubsequently extracted with aqueous LiCl (4% w/w), 0.1 M HCl and saturated aqueous NaHCO3
  2. dry with materialThe organic layer was dried over MgSO4
  3. customthe solvent was removed under reduced pressure
  4. customto give the crude which

Sources & evidence

ORD record
ord-ab8cb3eac6014212aca8b2bdf14a801b
Source dataset
uspto-grants-2013_04
Patent number
US08426420B2

Reaction notes

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