Reaktion #427361

ord-a3e45ccfceb946e8a893cac88bb13f32

Reaktionsgleichung

C[C@H]1NC(=S)[C@@H](NC(=O)OC(C)(C)C)C[C@H]1c1ccccc1
tert-butyl[(3S,5S,6R)-6-methyl-5-phenyl-2-thioxopiperidin-3-yl]carbamate
COC(C)(C)C(O)CN
1-amino-3-methoxy-3-methylbutan-2-ol
CCN(CC)CC
triethylamine
→
COC(C)(C)C(O)CN=C1N[C@H](C)[C@H](c2ccccc2)C[C@@H]1NC(=O)OC(C)(C)C
crude title compound
COC(C)(C)C(O)CN=C1N[C@H](C)[C@H](c2ccccc2)C[C@@H]1NC(=O)OC(C)(C)C
tert-Butyl{(3S,5S,6R)-2-[(2-hydroxy-3-methoxy-3-methylbutyl)imino]-6-methyl-5-phenylpiperidin-3-yl}carbamate

Edukte

C[C@H]1NC(=S)[C@@H](NC(=O)OC(C)(C)C)C[C@H]1c1ccccc1
tert-butyl[(3S,5S,6R)-6-methyl-5-phenyl-2-thioxopiperidin-3-yl]carbamate
COC(C)(C)C(O)CN
1-amino-3-methoxy-3-methylbutan-2-ol
CCN(CC)CC
triethylamine

Reagenzien

[Cl][Hg][Cl]
mercury (II) chloride

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Einengenconcentrated

Vorschrift

To a solution of tert-butyl[(3S,5S,6R)-6-methyl-5-phenyl-2-thioxopiperidin-3-yl]carbamate (150 mg, 0.47 mmol) in ethanol (4.7 mL) was added 1-amino-3-methoxy-3-methylbutan-2-ol (156 mg, 1.17 mmol), mercury (II) chloride (165 mg, 0.61 mmol), and triethylamine (163 μL, 1.17 mmol). The mixture was stirred 20 min, and then concentrated, giving the crude title compound. MS 420.4 (M+1).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08895572B2uspto-grants-2014_11