Tetrahydrofuran → tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-(trimethylsilyl)benzyl)-4-morpholinecarboxylate

HRID 369805ノート

反応式

HRID 369805 の反応式
[O:1]=[C:2]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@@H:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:3]1.[CH3:27][Si:28]([CH3:38])([CH3:37])[C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[CH2:32]Br.C1COCC1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].C1COCC1>O>[O:1]=[C:2]1[C@H:7]([CH2:32][C:31]2[CH:34]=[CH:35][CH:36]=[C:29]([Si:28]([CH3:27])([CH3:38])[CH3:37])[CH:30]=2)[N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@@H:5]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C@@H:4]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[O:3]1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 981230tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylateHCID 12583977(3-(Bromomethyl)phenyl)trimethylsilaneHCID 23700795NaHMDS tetrahydrofuran

生成物 1

HCID 57318012tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-(trimethylsilyl)benzyl)-4-morpholinecarboxylate収率 88%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
-78 °C

実験手順

A dry 250 mL 3-necked flask equipped with a magnetic stirrer and a nitrogen inlet was charged with 2.08 g of t-butyl (2R, 3S)-(-)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate (Aldrich), 1.43 g of 3-(trimethylsilyl)benzyl bromide (Yamakawa, T., et al, J. Med. Chem., 1990, 33, 1430), and 45 mL of anhydrous THF. The solution was cooled to -78° C. and was treated with 6.17 mL of 1 M sodium bis(trimethylsilyl)amide/THF (Aldrich) via syringe through a rubber septum. The solution was stirred at -78° C. for 3.5 h and was then poured into 150 mL of water. The resulting mixture was extracted with EtOAc (4×50 mL). The combined EtOAc extracts were washed with saturated brine (3×100 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to give a light yellow oil. The crude material was purified by flash chromatography on silica gel (9:1 hexane:EtOAc) to afford 2.6 g (88%) of tert-butyl (2R, 3S, 5S)-6-oxo-2,3-diphenyl-5-(3-(trimethylsilyl)benzyl)-4-morpholinecarboxylate as a white powder, m.p. 88-90° C.

後処理

  1. customA dry 250 mL 3-necked flask equipped with a magnetic stirrer and a nitrogen inlet
  2. extractionThe resulting mixture was extracted with EtOAc (4×50 mL)
  3. washThe combined EtOAc extracts were washed with saturated brine (3×100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give a light yellow oil
  7. customThe crude material was purified by flash chromatography on silica gel (9:1 hexane:EtOAc)

出典と根拠

ORDレコード
ord-a4dd648636644ce280a67b90f958b977
出典データセット
uspto-grants-2000_10
特許番号
US06140100

反応ノート

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