Acetic Acid → Tert-butyl 4-((2-(2,4-dimethoxybenzylamino)pyridin-3-yl)methylamino)piperidine-1-carboxylate

HRID 1172295

Reaktionsgleichung

Reaktionsgleichung von HRID 1172295
[CH3:1][O:2][C:3]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:4]=1[CH2:5][NH:6][C:7]1[C:12]([CH2:13][NH2:14])=[CH:11][CH:10]=[CH:9][N:8]=1.O=[C:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[C:31]([O:30][C:28]([N:25]1[CH2:26][CH2:27][CH:22]([NH:14][CH2:13][C:12]2[C:7]([NH:6][CH2:5][C:4]3[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:3]=3[O:2][CH3:1])=[N:8][CH:9]=[CH:10][CH:11]=2)[CH2:23][CH2:24]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 222931603-(Aminomethyl)-N-(2,4-dimethoxybenzyl)pyridin-2-amine

Produkt 1

HCID 22293293Tert-butyl 4-((2-(2,4-dimethoxybenzylamino)pyridin-3-yl)methylamino)piperidine-1-carboxylateAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 10340Sodium CarbonateLösungsmittel

Versuchsvorschrift

To a stirred solution of N-(2,4-Dimethoxybenzyl)-3-(aminomethyl)pyridin-2-amine (2.04 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (0.41 g, 2.04 mmol) in DCE (8 ml) and AcOH (115 μL, 2.04 mmol) was added NaBH(OAc)3 (0.43 g, 2.04 mmol) and the reaction stirred at RT until judged complete by LCMS. The reaction mixture was diluted with DCM and sat. aq. Na2CO3, the layers were separated and the organic layer was dried (Na2SO3) and evaporated to dryness. Purification by column chromatography (MeOH/DCM) gave the desired product (0.64 g, 69%). LC/MS (10% to 99%): M/Z (M+H)+ (obs)=457; tR=2.19.

Aufarbeitung

  1. customthe layers were separated
  2. dry with materialthe organic layer was dried (Na2SO3)
  3. customevaporated to dryness
  4. customPurification by column chromatography (MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-32427160f2b647bca3fba4e710178cec
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834000B2

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