Phthalimide → (S)-(+)-N-(2,3-Epoxypropyl)phthalimide

HRID 12378

反応式

HRID 12378 の反応式
[O:1]1[CH2:3][C@@H:2]1[CH2:4]O.[C:6]1(=[O:16])[NH:10][C:9](=[O:11])[C:8]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:7]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[O:1]1[CH2:3][C@@H:2]1[CH2:4][N:10]1[C:6](=[O:16])[C:7]2[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:9]1=[O:11]

参加物

6

反応物 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6973630(-)-Glycidol

生成物 1

HCID 719412(S)-(+)-N-(2,3-Epoxypropyl)phthalimide収率 73.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a cold solution of (S)-1-oxiranylmethanol (5 g, 67.5 mmol) and phthalimide (9.9 g, 67.3 mmol) in tetrahydrofuran (200 mL) in ice bath was added triphenylphosphine (17.9 g, 68.2 mmol) and diethyl azodicarboxylate (12.3 g, 70.6 mmol). The mixture was stirred at 0° C. for 2 h and at ambient temperature for 48 h. The mixture was concentrated under vacuum, and the oily residue was purified by flash silica column chromatography, yielding the desired product (10.1 g) as pale yellow solid: Rf=0.51 in 1:1 EtOAc/hexane. 1H—NMR (CDCl3, 300 MHz): δ (ppm) 7.76-7.64 (m, 2H), 7.63-7.60 (m, 2H), 3.9-3.8 (dd, 1H), 3.70-3.65 (dd, 1H), 3.15 (m, 1H), 2.70-2.67 (dd, 1H), 2.58-2.55 (dd, 1H).

後処理

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe oily residue was purified by flash silica column chromatography

出典と根拠

ORDレコード
ord-0fb31da23a524499978fccaaf3c41b28
出典データセット
uspto-grants-2010_06
特許番号
US07728006B2

関連ノート

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