Reaktion #168296

ord-c2783cae4986471a86b78c8d8af456e8

Reaktionsgleichung

CC(C)(C)OC(=O)N1CC[C@@H](N(Cc2ccccc2)C(=O)CCl)[C@H](O)C1
trans-tert-butyl 4-[benzyl(chloroacetyl)amino]-3-hydroxypiperidine-1-carboxylate
[I-].[Na+]
NaI
→
CC(C)(C)OC(=O)N1CC[C@@H](N(Cc2ccccc2)C(=O)CI)[C@H](O)C1
trans-tert-butyl 4-[benzyl(iodoacetyl)amino]-3-hydroxypiperidine-1-carboxylate

Edukte

CC(C)(C)OC(=O)N1CC[C@@H](N(Cc2ccccc2)C(=O)CCl)[C@H](O)C1
trans-tert-butyl 4-[benzyl(chloroacetyl)amino]-3-hydroxypiperidine-1-carboxylate
[I-].[Na+]
NaI

Reagenzien

Keine

Lösungsmittel

CC#N
CH3CN

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturat reflux for 1 h
  2. 2
    Einengenconcentrated
  3. 3
    workup.DISSOLUTIONThe residue was dissolved in DCM (1 L)
  4. 4
    Filtrationfiltered
  5. 5
    EinengenThe filtrate was concentrated under reduced pressure

Vorschrift

To a solution of trans-tert-butyl 4-[benzyl(chloroacetyl)amino]-3-hydroxypiperidine-1-carboxylate (144 g, 376 mmol) in CH3CN (2 L) was added NaI (56.4 g, 376 mmol) in one portion. The mixture was stirred at reflux for 1 h and then concentrated. The residue was dissolved in DCM (1 L) and filtered. The filtrate was concentrated under reduced pressure to afford trans-tert-butyl 4-[benzyl(iodoacetyl)amino]-3-hydroxypiperidine-1-carboxylate, which was used directly in the next step without further purification.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08846657B2uspto-grants-2014_09