Allyl iodide → 1,2-Pyrrolidinedicarboxylic acid, 2-(2-propen-1-yl)-, 2-methyl 1-(phenylmethyl) ester

HRID 276756Notes

Reaction equation

HRID 276756 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[CH:20]([N-]C(C)C)([CH3:22])[CH3:21].[Li+].C(I)C=C.[Cl-].[NH4+]>C1COCC1>[CH2:22]([C:4]1([C:3]([O:2][CH3:1])=[O:19])[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[CH:20]=[CH2:21]

Participants

6

Reactant 4

HCID 11166Allyl iodideHCID 25517Ammonium ChlorideHCID 688168(S)-1-Benzyl 2-methyl pyrrolidine-1,2-dicarboxylateHCID 2724682Lithium diisopropylamide

Product 1

HCID 107095511,2-Pyrrolidinedicarboxylic acid, 2-(2-propen-1-yl)-, 2-methyl 1-(phenylmethyl) ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-benzyloxycarbonylproline methyl ester (13 g) in THF (20 ml) was added dropwise to lithium diisopropylamide (27.5 ml, 2M in hexane/THF) in THF (100 ml) at −78° C. under nitrogen. The mixture was stirred for 30 minutes and then allyl iodide (5.5 ml) was added dropwise and the mixture stirred for a further 30 minutes and then allowed to warm to ambient temperature. The mixture was then added to aqueous ammonium chloride (200 ml) and extracted with ether (2×200 ml). The ether layer was evaporated and the residue was purified by chromatography on silica using a gradient of hexane increasing to 20% ethyl acetate:hexane. The appropriate fractions, evaporated to dryness, gave methyl (RS)-2-allyl-N-(benzyloxycarbonyl)prolinate (9 g) as an oil.

Workup

  1. stirringthe mixture stirred for a further 30 minutes
  2. extractionextracted with ether (2×200 ml)
  3. customThe ether layer was evaporated
  4. customthe residue was purified by chromatography on silica using a gradient of hexane increasing to 20% ethyl acetate
  5. customThe appropriate fractions, evaporated to dryness

Sources & evidence

ORD record
ord-5c3bce02d1464bdda0cccf6ff707f1f9
Source dataset
uspto-grants-2002_03
Patent number
US06355617B1

Reaction notes

Loading…