Potassium Carbonate → (S)-2-[(5-Cyano-pyridin-2-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 18105

반응식

HRID 18105 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH2:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].C(N(C(C)C)CC)(C)C>C1(C)C(C)=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][NH:14][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 51520946-Chloro-3-pyridinecarbonitrile

생성물 1

HCID 67090650(S)-2-[(5-Cyano-pyridin-2-ylamino)-methyl]-pyrrolidine-1-carboxylic acid tert-butyl ester수율 44.2%

시약·촉매·용매 1

HCID 7237O-Xylene용매

실험 절차

(S)-2-Aminomethylpyrrolidine-1-carboxylic acid tert-butyl ester (0.3 g), 6-chloronicotinonitrile (0.21 g), potassium carbonate (0.41 g) and diisopropylethylamine (0.78 ml) were heated in xylene at 130° C. for 26 h, cooled and the mixture filtered through kieselguhr. The filtrate was evaporated and the residue chromatographed on silica gel, eluting with ethyl acetate-hexane mixtures to afford the title compound (0.2 g). Mass Spectrum (API+): Found 303 (MH+). C16H22N4O2 requires 302.

후처리

  1. temperaturecooled
  2. filtrationthe mixture filtered through kieselguhr
  3. customThe filtrate was evaporated
  4. customthe residue chromatographed on silica gel
  5. washeluting with ethyl acetate-hexane mixtures

출처 및 근거

ORD 기록
ord-10a904a3eba64466bb5d478119d5fb0d
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741329B2

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