Methyl iodide → HCID 58748311, compound

HRID 1162702Notes

Reaction equation

HRID 1162702 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]([C:14]#[N:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16]I>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][CH3:16])[C@H:10]([C:14]#[N:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 58748337trans-1-Boc-3-cyano-4-hydroxypyrrolidine

Product 1

HCID 58748311HCID 58748311, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

80.2 A suspension of (3S,4S)-3-cyano-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (212 mg) in 10 ml of THF and 2.32 g of Ag2O and 0.62 ml of CH3I was heated in a sealed tube to 50° C. for 16 h. The suspension was filtered and the filtrate chromatographed on silica (heptane/AcOEt, 3:1) to give 161 mg of (3S,4S)-3-cyano-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester. Colorless oil. MS 171.4 ([M-isobutene+H]+)

Workup

  1. filtrationThe suspension was filtered
  2. customthe filtrate chromatographed on silica (heptane/AcOEt, 3:1)

Sources & evidence

ORD record
ord-6f44fea281454aa29945c2c4c316cd01
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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