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

HRID 2355526Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2355526
[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-eb5ed33ddfce4f0ca878e5479e55601e
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754737B2

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