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

HRID 2220995ノート

反応式

HRID 2220995 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
70 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6b915e16bfbd4f27858f865960b7880f
出典データセット
uspto-grants-2008_05
特許番号
US07368453B2

反応ノート

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