Triphenylphosphine → N-(4-phenylbenzenesulfonyl)aziridine

HRID 1952434ノート

反応式

HRID 1952434 の反応式
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(N1C[C@@H:30](O)[C@H:29]([NH:33][S:34]([C:37]2[CH:42]=[CH:41][C:40]([C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[CH:39][CH:38]=2)(=[O:36])=[O:35])C1)(OC(C)(C)C)=O.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:43]1([C:40]2[CH:41]=[CH:42][C:37]([S:34]([N:33]3[CH2:30][CH2:29]3)(=[O:36])=[O:35])=[CH:38][CH:39]=2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

参加物

5

反応物 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 86654490(+/-)-N-Boc-trans-3-(4-phenylbenzenesulfonamido)-4-hydroxypyrrolidine

生成物 1

HCID 86654492N-(4-phenylbenzenesulfonyl)aziridine収率 145.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of Ph3P (242 mg, 0.92 mmol) and (±)-N-Boc-trans-3-(4-phenylbenzenesulfonamido)-4-hydroxypyrrolidine (350 mg, 0.84 mmol) in THF (20 mL) at 0° C. was added diethyl azodicarboxylate (DEAD) (160 μL, 1.0 mmol) dropwise. The reaction mixture was stirred at room temperature overnight, then it was evaporated under reduced pressure. The residue was purified by flash chromatography (30% ethyl acetate in hexane) to give the N-(4-phenylbenzenesulfonyl)aziridine (317 mg, 95%): 1H NMR (300 MHz, CDCl3) δ 8.01 (d, J=8, 2H), 7.76 (d, J=8, 2H), 7.62 (d, J=7, 2H), 7.48 (m, 3H), 3.73 (dd, J=12, 2, 2H), 3.64 (dd, J=6, 2, 1H), 3.53 (dd, J=6, 2, 1H), 3.40 (m, 2H), 1.42 (s, 9H); HRMS (ESI) calculated for C21H24N2O4SNa+ 423.1355. found 423.1355.

後処理

  1. customit was evaporated under reduced pressure
  2. customThe residue was purified by flash chromatography (30% ethyl acetate in hexane)

出典と根拠

ORDレコード
ord-207c8a69cae74ff3b256128035116047
出典データセット
uspto-grants-2013_03
特許番号
US08404866B2

反応ノート

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