(Bis(2-methoxyethyl)amino)sulfur trifluoride → 4-azidomethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 1972073Notes

Reaction equation

HRID 1972073 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][N:15]=[N+:16]=[N-:17])[C@H:10](O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COCCN(S(F)(F)F)CCOC>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]=[C:11]([CH2:14][N:15]=[N+:16]=[N-:17])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 86657830cis-4-Azidomethyl-1-tert-butoxycarbonyl-3-hydroxypiperidine

Product 1

HCID 866578344-azidomethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of cis (±)-4-azidomethyl-3-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (1.95 mmol, 0.5 g) was added bis(2-methoxyethyl)aminosulfur trifluoride (2.34 mmol, 0.52 g) slowly and stirred for 12. The reaction mixture was diluted with DCM (10 mL), washed with aq. NaHCO3 solution, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography using ethyl acetate:hexanes (2:8) to get 4-azidomethyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester.

Workup

  1. washwashed with aq. NaHCO3 solution
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash silica gel column chromatography

Sources & evidence

ORD record
ord-500967d508674b1cab8a0db00fa98401
Source dataset
uspto-grants-2013_04
Patent number
US08431575B2

Reaction notes

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