Sodium Bicarbonate → tert-Butyl trans(+/-)-4-amino-3-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate

HRID 1425009Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1425009
[N:1]([C@@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][C@H:5]1[NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])=[N+]=[N-].[BH4-].[Na+].C(=O)(O)[O-].[Na+]>C1COCC1.CO.O.O.[Ni](Cl)Cl>[NH2:1][C@@H:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][C@H:5]1[NH:17][C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]

Komponenten

7

Edukt 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 86648551tert-Butyl trans(+/-)-4-azido-3-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate

Produkt 1

HCID 86648550tert-Butyl trans(+/-)-4-amino-3-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 10942802Nickel chloride dihydrateKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

tert-Butyl trans(±)-4-azido-3-{[benzyloxy)carbonyl]amino}piperidine-1-carboxylate obtained in Example (79b) (265.6 mg, 0.71 mmol) was dissolved in THF (6 mL) and methanol (3 mL). Nickel chloride dihydrate (345 mg, 1.42 mmol) and sodium borohydride (117 mg, 2.85 mmol) were added under ice-cooling, and the mixture was heated to room temperature and stirred for 30 minutes. Saturated aqueous sodium bicarbonate solution was added to the reaction solution, followed by filtration through celite and extraction with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting compound was used for the next reaction without purification.

Aufarbeitung

  1. temperaturecooling
  2. filtrationfollowed by filtration through celite and extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting compound was used for the next reaction without purification

Quellen und Nachweise

ORD-Eintrag
ord-4a9ba0712850420a9916aa1f29b9198a
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927588B2

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