Dimethylformamide → 1,3-Dibenzyl (3RS,4SR)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylate

HRID 446034ノート

反応式

HRID 446034 の反応式
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([O:16][C:17]([N:19]1[CH2:23][CH:22]([CH3:24])[C:21]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])([C:25]([OH:27])=[O:26])[CH2:20]1)=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[C:32]([O:31][C:29](=[O:30])[CH2:28][C:21]1([C:25]([O:27][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:26])[CH:22]([CH3:24])[CH2:23][N:19]([C:17]([O:16][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:18])[CH2:20]1)([CH3:34])([CH3:33])[CH3:35]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 71293735(3RS,4SR)-1-[(Benzyloxy)carbonyl]-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-3-carboxylic acid

生成物 1

HCID 866782511,3-Dibenzyl (3RS,4SR)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylate収率 98.2%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
5 °C

実験手順

Benzyl bromide (4.48 ml, 37.7 mmol) was added to a mixture of (3RS,4SR)-1-[(benzyloxy)carbonyl]-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-3-carboxylic acid obtained in Reference Example 1b (14.5 g, 38.5 mmol), potassium carbonate (10.6 g, 77 mmol) and N,N-dimethylformamide (50 ml) with stirring under ice-cooling (internal temperature: 3 to 7° C.), and the mixture was stirred for one hour, returned to mom temperature and stirred overnight. Water was added to the reaction liquid, which was extracted with ethyl acetate three times. The organic layers were combined, sequentially washed with a saturated aqueous ammonium chloride solution (five times), water (twice) and brine, and then dried over sodium sulfate, filtered and concentrated to give the title compound (17.67 g, yield: 98.2%).

後処理

  1. stirringthe mixture was stirred for one hour
  2. stirringstirred overnight
  3. extractionwas extracted with ethyl acetate three times
  4. washsequentially washed with a saturated aqueous ammonium chloride solution (five times), water (twice) and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-d09bee670b6d48cfb1eafed9b9e09818
出典データセット
uspto-grants-2013_07
特許番号
US08476301B2

反応ノート

読み込み中…