Methyl iodide → trans-3-Azido-1-Boc-4-methoxypyrrolidine

HRID 1162635Notes

Reaction equation

HRID 1162635 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[C@@H:10]([N:14]=[N+:15]=[N-:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].I[CH3:18]>C(#N)C.C1COCC1.[Ag-]=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][CH3:18])[C@@H:10]([N:14]=[N+:15]=[N-:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 6328Methyl iodide2×HCID 11128048trans-3-Azido-1-Boc-4-hydroxypyrrolidine

Product 1

HCID 11817353trans-3-Azido-1-Boc-4-methoxypyrrolidine

Reagents, catalysts & solvents 3

HCID 178418778HCID 178418778, compoundCatalyst2×HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

24.1 A solution of 1.0 g (3S,4S)-3-azido-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (example 22.2) in 15 ml acetonitrile and 3 ml THF was treated with 3.0 g silver(I) oxide and and 2.7 ml iodomethane. The reaction mixture was stirred over night at r.t., then again treated with 3.0 g silver(I) oxide and 2.7 ml iodomethane. The reaction was agitated over night at r.t., then filtrated. The filtrate was concentrated. The crude product was purified by chromatography (silica gel; cyclohexane/EtOAc 2:1) to give 1.0 g (3S,4S)-3-azido-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester as light yellow oil. MS 243.4 ([M+H]+)

Workup

  1. stirringThe reaction was agitated over night at r.t.
  2. filtrationfiltrated
  3. concentrationThe filtrate was concentrated
  4. customThe crude product was purified by chromatography (silica gel; cyclohexane/EtOAc 2:1)

Sources & evidence

ORD record
ord-d48bb62db5f34874972aaaef32d95e29
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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