Triphenylphosphine → N-(4-phenylbenzenesulfonyl)aziridine

HRID 1952434Notes

Reaction equation

HRID 1952434 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-207c8a69cae74ff3b256128035116047
Source dataset
uspto-grants-2013_03
Patent number
US08404866B2

Reaction notes

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