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

HRID 1172295

반응식

HRID 1172295 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매HCID 10340Sodium Carbonate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-32427160f2b647bca3fba4e710178cec
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834000B2

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