2-Naphthalenecarboxaldehyde → (S)-2-{[(Naphthalen-2-ylmethyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 2220710노트

반응식

HRID 2220710 반응식
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=O.[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH2:25][NH2:26])=[O:19])([CH3:16])([CH3:15])[CH3:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][C@H:21]1[CH2:25][NH:26][CH2:11][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

참가 물질

5

반응물 3

HCID 62012-NaphthalenecarboxaldehydeHCID 1512533tert-Butyl (2S)-2-(aminomethyl)pyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 59772986(S)-2-{[(Naphthalen-2-ylmethyl)-amino]-methyl}-pyrrolidine-1-carboxylic acid tert-butyl ester수율 58.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Experimental conditions were analogous to Example 1. 0.27 g (1.76 mmol) of naphthalene-2-carbaldehyde, 0.35 g (1.76 mmol) of (S)-2-aminomethyl-pyrrolidine-1-carboxylic acid tert-butyl ester, were dissolved in 10 mL dichloromethane, and 0.55 g (2.64 mmol) of sodium triacetoxyborohydride was added. The reaction was quenched with aqueous sodium bicarbonate. The residue from the organic layer was purified using flash chromatography (ethyl acetate in hexane), yielded to 350 mg of the free base as colorless oil. LC-MSD, m/z for C21H28N2O2 [M+H]+: 341.2

후처리

  1. customThe reaction was quenched with aqueous sodium bicarbonate
  2. customThe residue from the organic layer was purified

출처 및 근거

ORD 기록
ord-e42a006ecdbc4501ba954f4b0b7963c0
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417062B2

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