Dimethylformamide dimethyl acetal → HCID 86594339, compound

HRID 1374535Notes

Reaction equation

HRID 1374535 reaction equation
CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[C:9]([C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])(=[O:11])[NH2:10]>CCCCCC>[CH3:3][N:4]([CH:6]=[N:10][C:9]([C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18])=[O:11])[CH3:5]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 6950961cbz-l-prolinamide

Product 1

HCID 86594339HCID 86594339, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
120 °C

Procedure

Part A: N,N-Dimethylformamide dimethyl acetal (5 mL) was added to benzyl (2S)-2-carbamoyl-pyrrolidine-1-carboxylate (1.05 g, 4.23 mmol) at ambient temperature. The resulting slurry was heated to 120° C. for 2 h then allowed to cool and poured into hexane (50 mL). The solvents were removed under reduced pressure yielding benzyl (2S)-2-(dimethylaminomethylenecarbamoyl)pyrrolidine-1-carboxylate as a colorless oil (1.35 g, crude quantative yield). HPLC (method 1) tR=1.70 min, Purity 100%; LCMS (method 4) tR=0.94 min, m/z 304 (M+1)

Workup

  1. temperatureto cool
  2. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-55b7f07005e947d2a2ef601982c380d0
Source dataset
uspto-grants-2007_01
Patent number
US07166586B2

Reaction notes

Loading…