Potassium Carbonate → (S)-benzyl 1-(2-tert-butoxy-2-oxoethyl)pyrrolidine-2-carboxylate

HRID 70882

反応式

HRID 70882 の反応式
Cl.[NH:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8].C([O-])([O-])=O.[K+].[K+].Br[CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26]>CN(C=O)C>[C:28]([O:27][C:25](=[O:26])[CH2:24][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])([CH3:31])([CH3:30])[CH3:29]

参加物

5

反応物 3

HCID 11430Potassium Carbonate2 回HCID 79177tert-Butyl bromoacetateHCID 2733413Proline benzyl ester hydrochloride

生成物 1

HCID 59607548(S)-benzyl 1-(2-tert-butoxy-2-oxoethyl)pyrrolidine-2-carboxylate収率 49.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of (S)-benzyl pyrrolidine-2-carboxylate hydrochloride (700 mg, 2.90 mmol) and K2CO3 (1201 mg, 8.69 mmol) in DMF (7 ml), t-butyl bromoacetate (0.535 ml, 3.62 mmol) is added. After stirring for 71 hours, aqueous K2CO3 (1.5 g of K2CO3/40 ml of H2O) is added to the reaction mixture. The products are extracted with EtOAc. The organic layer is washed twice with water and once with brine, dried over K2CO3, filtered, and concentrated to give (S)-benzyl 1-(2-tert-butoxy-2-oxoethyl)pyrrolidine-2-carboxylate (458 mg); HPLC retention time=1.38 minutes (condition D); MS (m+1)=320.2; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.44 (s, 9 H) 1.81-2.03 (m, 3 H) 2.13-2.14 (m, 1 H) 2.82-2.88 (m, 1 H) 3.13-3.17 (m, 1 H) 3.46 (A of AB, J=17.3 Hz, 1 H) 3.49 (B of AB, J=17.3 Hz, 1 H) 3.73 (dd, J=8.8 and 4.8 Hz, 1 H) 5.15 (A of AB, J=12.4 Hz, 1 H) 5.17 (B of AB, J=12.4 Hz, 1 H) 7.29-7.38 (m, 5 H).

後処理

  1. additionis added
  2. extractionThe products are extracted with EtOAc
  3. washThe organic layer is washed twice with water and once with brine
  4. dry with materialdried over K2CO3
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-e5818882a6164ceba0db737e26bdcea1
出典データセット
uspto-grants-2014_09
特許番号
US08822534B2

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