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

HRID 2220710ノート

反応式

HRID 2220710 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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

後処理

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

出典と根拠

ORDレコード
ord-e42a006ecdbc4501ba954f4b0b7963c0
出典データセット
uspto-grants-2008_08
特許番号
US07417062B2

反応ノート

読み込み中…