Lithium Hydroxide → 1-(Cyanomethyl)-L-proline

HRID 1257638Notes

Reaction equation

HRID 1257638 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[CH2:10][C:11]#[N:12])=[O:4].[OH-].[Li+]>C1COCC1>[C:11]([CH2:10][N:6]1[CH2:7][CH2:8][CH2:9][C@H:5]1[C:3]([OH:4])=[O:2])#[N:12]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 30491532Methyl 1-(cyanomethyl)-L-prolinate

Product 1

HCID 341784361-(Cyanomethyl)-L-proline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-1-cyanomethyl-pyrrolidine-2-carboxylic acid methyl ester (100 mg, 0.60 mmol) and lithium hydroxide (16 mg, 0.66 mmol) in THF (2 mL) was stirred at ambient temperature for 16 hours. The reaction mixture was concentrated under vacuum and the resulting residue dissolved in water (5 mL) and neutralized with 1M aqueous HCl. The resulting solution was freeze-dried to afford (S)-1-cyanomethyl-pyrrolidine-2-carboxylic acid. 1H NMR (300 MHz, CDCl3) δ: 3.80 (d, 2H), 3.53 (dd, 1H), 3.25 (m, 1H), 2.85 (m, 1H), 2.40-1.94 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionthe resulting residue dissolved in water (5 mL)
  3. customThe resulting solution was freeze-dried

Sources & evidence

ORD record
ord-caf791d9b9814345b34c688557aaf683
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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