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

HRID 1695894Notes

Reaction equation

HRID 1695894 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-ffad3d33c3cb40ee9e5a44c7f7633769
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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