Hydrochloric Acid → HCID 55299026, compound

HRID 1813994Notes

Reaction equation

HRID 1813994 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C@@H:6]1[CH2:10][CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7]1)=[O:4].Cl.O1CCOCC1>C(Cl)Cl>[CH3:1][NH:2][C:3]([NH:5][C@@H:6]1[CH2:10][CH2:9][NH:8][CH2:7]1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 69840849HCID 69840849, compound

Product 1

HCID 55299026HCID 55299026, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl-(3R)-3-{[(methylamino)carbonyl]amino}pyrrolidine-1-carboxylate 6-3 (2.174 g, 8.93 mmol) was dissolved in 3 mL CH2Cl2 and the solution was cooled to 0° C. 4.0M HCl in dioxane (33.50 mL, 134.0 mmol) was added and the solution was allowed to warm to room temperature. After 4.5 hours the reaction was concentrated in vacuo to afford N-methyl-N′-[(3R)-pyrrolidin-3-yl]urea 6-4 as an off-white solid. HCl salt: 1H NMR (DMSO-d6) δ 9.13 (bs, 2H), 4.15 (m, 1H), 3.10-3.3.29 (m, 3H), 2.96-2.87 (m, 1H), 2.54 (s, 3H), 2.13-2.01 (m, 1H), 1.75 (m, 1H).

Workup

  1. temperatureto warm to room temperature
  2. concentrationAfter 4.5 hours the reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-c47701152c404aca8d6a5b75c826457d
Source dataset
uspto-grants-2005_04
Patent number
US06875767B2

Reaction notes

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