Sodium borohydride → (3R,4R)-benzyl 3-amino-4-(tosyloxy)piperidine-1-carboxylate

HRID 1254409Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1254409
[BH4-].[Na+].[N:3]([C@H:6]1[C@H:11]([O:12][S:13]([C:16]2[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10][CH2:9][N:8]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:7]1)=[N+]=[N-]>CO>[NH2:3][C@H:6]1[C@H:11]([O:12][S:13]([C:16]2[CH:17]=[CH:18][C:19]([CH3:20])=[CH:21][CH:22]=2)(=[O:14])=[O:15])[CH2:10][CH2:9][N:8]([C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[O:24])[CH2:7]1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydride2×HCID 59201561HCID 59201561, Verbindung

Produkt 1

HCID 59201320(3R,4R)-benzyl 3-amino-4-(tosyloxy)piperidine-1-carboxylateAusbeute 64,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a cooled (0° C., ice/water bath) solution of CuSO4.5H2O (642 mg, 0.5 equiv) in methanol (30 mL) was added slowly NaBH4 (200 mg, 1.05 equiv). To the stirred black suspension was added a solution of (3R,4R)-benzyl 3-azido-4-(tosyloxy)piperidine-1-carboxylate (2.21 g, 5.14 mmol) in methanol (20 mL). Additional NaBH4 (578 mg, 3 equiv) was introduced into the reaction in four portions over the course of 1 h. LC-MS showed the reaction was complete. The reaction mixture was filtered through a pad of Celite, and concentrated. The residue was diluted with CH2Cl2 (70 mL), washed with water (15 mL), satd aq NH4Cl solution (2×10 mL) and brine (15 mL), and dried over Na2SO4. Concentration afforded (3R,4R)-benzyl 3-amino-4-(tosyloxy)piperidine-1-carboxylate (1.34 g, 64%). LC-MS (3 min) tR=1.26 min., m/z 405 (M+1). The product was used for the next step without further purification.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. concentrationconcentrated
  3. additionThe residue was diluted with CH2Cl2 (70 mL)
  4. washwashed with water (15 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationConcentration

Quellen und Nachweise

ORD-Eintrag
ord-c6b6921da89043ee8178665c387f45f6
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455521B2

Notizen zur Reaktion

Wird geladen…