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

HRID 2288055
Notes
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Reaction equation

HRID 2288055 reaction equation
[CH2:1]([C:4]1([C:19]([OH:21])=[O:20])[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:2]=[CH2:3].[Li].[CH2:23](I)C=C.[Cl-].[NH4+]>C1COCC1.CCCCCC.C1COCC1>[CH2:1]([C:4]1([C:19]([O:21][CH3:23])=[O:20])[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:2]=[CH2:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11166Allyl iodideHCID 25517Ammonium ChlorideHCID 3028194LithiumHCID 106848391-[(Benzyloxy)carbonyl]-2-(prop-2-en-1-yl)pyrrolidine-2-carboxylic acid

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
2×
HCID 21883165Tetrahydrofuran hexaneSolvent

Procedure

Synthesis of (RS)-2-allyl-N-(benzyloxycarbonyl)proline ##STR5## N-benzyloxycarbonylproline methyl ester (13 g) in THF (20 ml) was added dropwise to lithium dilsopropylamide (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-4b107ba6106644c4b326fe1f441f10e2
Source dataset
uspto-grants-2000_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06087336

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes