Methyl Isocyanate → Benzyl 4-{1-[(methylamino)carbonyl]pyrrolidin-3-yl}piperazine-1-carboxylate

HRID 1241418Notes

Reaction equation

HRID 1241418 reaction equation
[NH:1]1[CH2:5][CH2:4][CH:3]([N:6]2[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[CH2:8][CH2:7]2)[CH2:2]1.CCN(C(C)C)C(C)C.[CH3:31][N:32]=[C:33]=[O:34]>C(Cl)Cl>[CH3:31][NH:32][C:33]([N:1]1[CH2:5][CH2:4][CH:3]([N:6]2[CH2:11][CH2:10][N:9]([C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])[CH2:8][CH2:7]2)[CH2:2]1)=[O:34]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 81531DiisopropylethylamineHCID 21934646Benzyl 4-(pyrrolidin-3-yl)piperazine-1-carboxylate

Product 1

HCID 21934712Benzyl 4-{1-[(methylamino)carbonyl]pyrrolidin-3-yl}piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

45-3 (0.27 g, 0.93 mmol) was dissolved in methylene chloride (4 mL) and DIEA (0.60 g, 4.67 mmol) and then a methylene chloride solution (1 mL) of methylisocyanate (0.050 g, 0.93 mmol) was added. The solution was then stirred for 30 minutes, after which it was concentrated and purified on a C18 preparative hplc column to afford 45-4. 1H-NMR (CD3OD): 7.37(m, 5H); 5.17(s, 2H); 3.89(m, 4H); 3.59(m, 4H); 3.36(m, 5H); 2.74(s, 3H); 2.47(m, 1H); 2.24(m, 1H).

Workup

  1. concentrationafter which it was concentrated
  2. custompurified on a C18 preparative hplc column
  3. customto afford 45-4

Sources & evidence

ORD record
ord-2123b7dd04d34171be46c2d64bac2f91
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

Loading…