Triphenylphosphine → N-(4-phenylbenzenesulfonyl)aziridine

HRID 1952434노트

반응식

HRID 1952434 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 86654492N-(4-phenylbenzenesulfonyl)aziridine수율 145.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-207c8a69cae74ff3b256128035116047
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08404866B2

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