tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylate → tert-butyl (2R,3S,5S)-6-oxo-2,3-diphenyl-5-(3-(3-pentyl)benzyl)4-morpholinecarboxylate

HRID 429917

反応式

HRID 429917 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][CH2:28][CH:29]([C:32]1[CH:33]=[C:34]([CH:37]=[CH:38][CH:39]=1)[CH2:35]Br)[CH2:30][CH3:31].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[O:1]=[C:2]1[C@H:7]([CH2:35][C:34]2[CH:37]=[CH:38][CH:39]=[C:32]([CH:29]([CH2:30][CH3:31])[CH2:28][CH3:27])[CH:33]=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

5

反応物 3

HCID 981230tert-butyl (2R,3S)-6-oxo-2,3-diphenylmorpholine-4-carboxylateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 54104700HCID 54104700、化合物

生成物 1

HCID 57256884tert-butyl (2R,3S,5S)-6-oxo-2,3-diphenyl-5-(3-(3-pentyl)benzyl)4-morpholinecarboxylate収率 48%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

According to example 142, 3.27 g of tert-butyl (2R, 3S)-(−)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate was alkylated with 2.23 g of 3-(3-pentyl)benzyl bromide in 70 mL of anhydrous TBF using 9.71 mL of 1 M sodium bis(trimethylsilyl)amide in THF. The crude product was subjected to flash chromatography on silica gel (9:1 hexane:EtOAc) and then recrystallization from EtOH-water to afford 2.26 g (48%) of tert-butyl (2R,3S,5S)-6-oxo-2,3-diphenyl-5-(3-(3-pentyl)benzyl)4-morpholinecarboxylate as a white crystalline solid, m.p. 143-144° C.

後処理

  1. customrecrystallization from EtOH-water

出典と根拠

ORDレコード
ord-883e7379d6ae44e8a3da43f6c082500b
出典データセット
uspto-grants-2001_11
特許番号
US06319702B1

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