1,2-Dichloroethane → (2R)-2-(morpholine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 478934

반응식

HRID 478934 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[C:13]([N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)=[O:15])=[O:7])([CH3:2])([CH3:3])[CH3:4]

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

생성물 1

HCID 69832143(2R)-2-(morpholine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester수율 63%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(2R)-Pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (2.15 g, 10 mmol) reacted with morpholine (1.3 mL, 15 mmol) in CH2Cl2 (30 mL) in the presence EDC (2.7 g, 15 mmol), HOBT (1.9 g, 15 mmol) and Et3N (2.1 mL, 15 mmol) at r.t. for 14 h. The mixture was evaporated to dryness and purified by column chromatography. After washing the resulting solid with aqueous NaHCO3 followed by H2O to remove HOBT contamination, pure compound (2R)-2-(morpholine-4-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 11a (1.79 g, 63%) was obtained.

후처리

  1. customThe mixture was evaporated to dryness
  2. custompurified by column chromatography
  3. washAfter washing the resulting solid with aqueous NaHCO3
  4. customto remove HOBT contamination

출처 및 근거

ORD 기록
ord-cb98b0ab204440b8b8bbdb6d68f3c7fd
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642232B2

연결된 노트

불러오는 중…