Methyl iodide → HCID 11002744, compound

HRID 490658Notes

Reaction equation

HRID 490658 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].P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C[I:50]>C1COCC1>[CH3:16][O:15][C:13]([C@@H:12]1[CH2:11][C@H: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 iodide2×HCID 11776TriphenylphosphineHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 5462977Diethyl azodicarboxylate

Product 1

HCID 11002744HCID 11002744, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a round-bottom flask equipped with a magnetic stir bar and an addition funnel under N2 was added N-Boc-L-trans-4-hydroxy-proline methyl ester (60 mmol, 1 equiv), P(Ph)3 (72 mmol, 1.2 equiv) and anhydrous THF (275 ml). The solution was cooled to 0 centigrade, DEAD (1.2 equiv) in dry THF was added dropwise; followed by the addition of MeI (1.2 equiv). Upon addition of MeI, the solution turned from dark brown to bright yellow. The reaction mixture was allowed to warm to ambient temperature and stirred for 10 hours. The solvent was removed under reduced pressure and the crude oil was purified by chromatography on silica gel to afford title product (19.44 g) as colorless oil in 91% yield. MS m/e=356.4 [M+H]+.

Workup

  1. customTo a round-bottom flask equipped with a magnetic stir bar and an addition funnel under N2
  2. temperatureThe solution was cooled to 0 centigrade
  3. customThe solvent was removed under reduced pressure
  4. customthe crude oil was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-4f30052409044b9d929d1b4ae7c3a1a3
Source dataset
uspto-grants-2009_05
Patent number
US07528136B2

Reaction notes

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