Tetrahydrofuran → (S)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamate

HRID 619835Notes

Reaction equation

HRID 619835 reaction equation
[C:1]([C@@H](C)C(N)(N)C(O)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.O[C:24]1[C:32]2[N:31]=N[NH:29][C:28]=2C=C[CH:25]=1.C1C[O:36]CC1>>[C:4]([O:3][C:1](=[O:2])[NH:31][C@H:32]1[CH2:24][CH2:25][NH:29][C:28]1=[O:36])([CH3:5])([CH3:6])[CH3:7]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 86752309(S)-Boc-Diaminobutyric acidHCID 178418300HCID 178418300, compound

Product 1

HCID 10750535(S)-tert-Butyl (2-oxopyrrolidin-3-yl)carbamate

Conditions

Temperature
60 °C

Procedure

(S)-Boc-Diaminobutyric acid (25 g, 115 mmol), triethyl amine (35 g, 344 mmol), and hydroxybenzotriazole (19.3 g, 143 mmol) are dissolved in 300 mL of THF. 1-(3-Dimethylaminopropyl)-3-ethylcarbodiiimide hydrochloride (27.4 g, 143 mmol) is added to the solution. The solution is heated to 60° C. over 15 minutes. A white precipitate forms and the solution is kept at 60° C. for 4 hours. After this time, the solution is filtered and the collected liquid is concentrated. The crude product is purified by column chromatography in a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2 to afford the title compound (19.6 g, 98 mmol) as a white solid.

Workup

  1. filtrationAfter this time, the solution is filtered
  2. concentrationthe collected liquid is concentrated
  3. customThe crude product is purified by column chromatography in a gradient of 1% MeOH/CH2Cl2 to 3% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-550887420a3f4a9a9df8c431932d9096
Source dataset
uspto-grants-1999_09
Patent number
US05958918

Reaction notes

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