Piperidine → (R)-tert-butyl 6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

HRID 1444713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1444713
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C@H:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:8][CH2:7][CH2:6]2)=O.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[N:21]1([CH2:1][C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[C@H:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:8][CH2:7][CH2:6]3)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Komponenten

6

Edukt 3

HCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 56594896(R)-tert-butyl 6-formyl-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

Produkt 1

HCID 56594897(R)-tert-butyl 6-(piperidin-1-ylmethyl)-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

In 100 mL of 1,2-dichloroethane, 5.0 g (18 mmol) of (R)-tert-butyl 6-formyl-1,2,3,4-tetrahydronaphthalen-1-ylcarbamate and 3.1 g (36 mmol) of piperidine were combined. Next, 7.6 g (36 mmol) of sodium triacetoxy borohydride was added and the mix was stirred under nitrogen overnight. The mix was then dissolved in 100 mL of ethyl acetate, washed with 25 mL of saturated sodium bicarbonate, washed with 25 mL of brine, dried with sodium sulfate and concentrated to yield the crude material.

Aufarbeitung

  1. washwashed with 25 mL of saturated sodium bicarbonate
  2. washwashed with 25 mL of brine
  3. dry with materialdried with sodium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a4e70acb009447198e41000c62bb26fc
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07662811B2

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