Trimethylsilyl isocyanate → 3-Hydroxypyrrolidine-1-carboxamide

HRID 2100428Notes

Reaction equation

HRID 2100428 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][NH:4][CH2:3]1.C[Si]([N:11]=[C:12]=[O:13])(C)C>C(O)(C)C>[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:12]([NH2:11])=[O:13])[CH2:3]1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 982104-Hydroxypyrrolidine

Product 1

HCID 120118413-Hydroxypyrrolidine-1-carboxamideYield 60%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of 3-hydroxypyrrolidine (1.0 g, 11.48 mmol) in isopropanol (27 mL) at rt was added trimethylsilylisocyanate (2.14 mL, 16.07 mmol) and the resulting solution stirred overnight. The resulting suspension was filtered and the residue washed with isopropanol and dried to give 3-hydroxy-pyrrolidine-1-carboxylic acid amide (0.89 g, 60%); 1H-NMR (300 MHz, d6-DMSO) 5.64 (2H, s), 4.85 (1H, d), 4.21-4.22 (1H, m), 3.22-3.28 (3H, m), 3.06-3.10 (1H, m), 1.79-1.90 (1H, m), 1.67-1.76 (1H, m).

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe residue washed with isopropanol
  3. customdried

Sources & evidence

ORD record
ord-a0c5c55eb0b14a7a9e8b7a90cf23c883
Source dataset
uspto-grants-2009_08
Patent number
US07572794B2

Reaction notes

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