Triethylamine → 2-[2-(1-methoxycarbonyl-(S)-ethylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 1441719ノート

反応式

HRID 1441719 の反応式
[CH3:1][O:2][C:3]([C:5]1([CH2:17][CH:18]=O)[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:4].Cl.[CH3:21][O:22][C:23](=[O:27])[C@H:24]([CH3:26])[NH2:25].C(N(CC)CC)C.C([BH3-])#N.[Na+]>C1(C)C=CC=CC=1.CO>[CH3:1][O:2][C:3]([C:5]1([CH2:17][CH2:18][NH:25][C@H:24]([C:23]([O:22][CH3:21])=[O:27])[CH3:26])[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])=[O:4]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 2733257Alanine methyl ester hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 738300911-Tert-butyl 2-methyl 2-(2-oxoethyl)pyrrolidine-1,2-dicarboxylate

生成物 1

HCID 686800982-[2-(1-methoxycarbonyl-(S)-ethylamino)-ethyl]-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1140Toluene溶媒

実験手順

271 mg (1 mmol) 2-(2-oxo-ethyl)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester and 154 mg (1.1 mmol) L-alanine methyl ester hydrochloride are suspended in 10 mL toluene and treated with 0.073 mL (1 eq.) triethylamine. The reaction mixture is stirred 10 minutes at room temperature and slowly evaporated in a rotary evaporator. The residue is taken up in 15 mL acetonitrile and 95 mg (1.5 mmol) sodium cyanoborohydride in 2 mL methanol added dropwise. Upon completion of the reaction (TLC, EtOAc/petroleum ether 4:1), the reaction mixture is evaporated and the residue taken up in ethyl acetate and treated with an ice-cold, saturated aqueous ammonium chloride solution, then extracted with ethyl acetate and saturated aqueous sodium bicarbonate. The combined organic phases are dried over sodium sulfate, filtered and evaporated to yield the crude desired product as a thick oil.

後処理

  1. customslowly evaporated in a rotary evaporator
  2. customthe reaction mixture is evaporated
  3. additiontreated with an ice-cold, saturated aqueous ammonium chloride solution
  4. extractionextracted with ethyl acetate and saturated aqueous sodium bicarbonate
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-dcea2c0cb6b8418eb7fa0a18b9e7af1a
出典データセット
uspto-grants-2010_02
特許番号
US07655686B2

反応ノート

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