Trimethylsilyl isocyanate → (R)-tert-butyl 3-ureidopyrrolidine-1-carboxylate

HRID 57541Notes

Reaction equation

HRID 57541 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[Si]([N:18]=[C:19]=[O:20])(C)(C)C.CCN(C(C)C)C(C)C>ClCCl>[NH:1]([C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1)[C:19]([NH2:18])=[O:20]

Participants

5

Reactant 3

HCID 70696Trimethylsilyl isocyanateHCID 81531DiisopropylethylamineHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidine

Product 1

HCID 71113416(R)-tert-butyl 3-ureidopyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-tert-butyl 3-aminopyrrolidine-1-carboxylate (180 mg, 1 mmol) in dichloromethane was added TMS-NCO (1 g, 8.7 mmol) and DIPEA (1.2 g, 10 mmol). The mixture was stirred at room temperature overnight, then was concentrated in vacuo. The residue was treated with EtOAc/H2O, the organic layer was combined, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give the crude title compound.

Workup

  1. concentrationwas concentrated in vacuo
  2. additionThe residue was treated with EtOAc/H2O
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-03b908eb6c974305becfdd62d3cb84c4
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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