Lithium borohydride → tert-Butyl (2R,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 2220995노트

반응식

HRID 2220995 반응식
[Li+].[BH4-].[OH:3][C@H:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@@H:6]([C:16](OC)=[O:17])[CH2:5]1>C1COCC1>[OH:3][C@H:4]1[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[C@@H:6]([CH2:16][OH:17])[CH2:5]1

참가 물질

4

반응물 2

HCID 4148881Lithium borohydrideHCID 6951202(2R,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

생성물 1

HCID 10680283tert-Butyl (2R,4R)-4-hydroxy-2-(hydroxymethyl)pyrrolidine-1-carboxylate수율 57.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
70 °C

실험 절차

LiBH4 (6.46 mmol as a solution in THF) was added to an ice cooled solution of (1,1-dimethylethyl) 2-methyl(2R,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate (0.36 g, 1.47 mmol) in THF. The reaction was heated at 70° C. for 48 hours. The reaction was quenched with isopropanol and then saturated NaHCO3. The mixture was diluted with water and extracted twice with ethyl acetate. The organic layers were washed with 1N NaOH, dried over MgSO4 and concentrated to give 0.185 g of the title compound. 1H NMR 400 MHz, DMSO-D6) δ ppm 1.4 (m, 9 H), 1.8 (m, 1 H), 2.0 (m, 1 H), 3.0 (m, 1 H), 3.4 (m, 1 H), 3.5 (m, 2 H), 3.7 (m, 1 H), 4.1 (m, 1 H), 4.9 (dd, J=5.3, 5.3 Hz, 1 H), 5.1 (m, 1 H).

후처리

  1. customThe reaction was quenched with isopropanol
  2. additionThe mixture was diluted with water
  3. extractionextracted twice with ethyl acetate
  4. washThe organic layers were washed with 1N NaOH
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6b915e16bfbd4f27858f865960b7880f
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07368453B2

반응 노트

불러오는 중…