Methyl iodide → 4-Iodo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 490583Notes

Reaction equation

HRID 490583 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[C@H:12]([C:13]([O:15][CH3:16])=[O:14])[CH2:11][C@@H:10](O)[CH2:9]1)=[O:7])([CH3:4])[CH3:3].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O.C[I:50]>C1COCC1>[CH3:16][O:15][C:13]([CH:12]1[CH2:11][CH:10]([I:50])[CH2:9][N:8]1[C:6]([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:7])=[O:14]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11776TriphenylphosphineHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 675472144-Iodo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a round-bottom flask equipped with a magnetic stir bar and an addition funnel under N2 is added N-Boc-L-trans-4-hydroxy-proline methyl ester, PPh3 and anhydrous THF. The solution is cooled to 0 centigrade, DEAD in THF is added; followed by the addition of MeI. The reaction mixture is allowed to warm to ambient temperature and stirred for about 10 hours. The solvent is removed and the crude product is purified to afford 4-iodo-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (31).

Workup

  1. customTo a round-bottom flask equipped with a magnetic stir bar and an addition funnel under N2
  2. temperatureThe solution is cooled to 0 centigrade
  3. customThe solvent is removed
  4. customthe crude product is purified

Sources & evidence

ORD record
ord-289436ba6f3044799cabff8cb406d201
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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