Triphenylphosphine → HCID 86654476, compound

HRID 1952429Notes

Reaction equation

HRID 1952429 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]([O:43][C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[CH:39][CH:38]=2)(=[O:36])=[O:35])C1)(OC(C)(C)C)=O.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[O:43]([C:40]1[CH:41]=[CH:42][C:37]([S:34]([N:33]2[CH2:30][CH2:29]2)(=[O:36])=[O:35])=[CH:38][CH:39]=1)[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 67232863HCID 67232863, compound

Product 1

HCID 86654476HCID 86654476, compoundYield 147%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of Ph3P (0.88 g, 3.35 mmol) and (±)-N-Boc-trans-3-(4-phenoxybenzenesulfonamido)-4-hydroxypyrrolidine (1.316 g, 3.04 mmol) in THF (20 mL) at 0° C. was added diethyl azodicarboxylate (DEAD) (0.58 mL, 3.33 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-phenoxybenzenesulfonyl)aziridine as a solid (1.23 g, 98%): mp 136-138° C.; 1H NMR (300 MHz, CDCl3) δ 7.88 (m, 2H), 7.43 (m, 2H), 7.22 (m, 1H), 7.10 (m, 4H), 3.72 (m, 2H), 3.59 (m, 1H), 3.47 (m, 1H), 3.38 (m, 2H), 1.42 (s, 9H); MS, ESI m/e 416.1 (M+); HRMS (ESI) calcd for C21H24N2O5SNa+ 439.1290. found 439.1290.

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-ad691c225bee4304a3b222238e5d0b23
Source dataset
uspto-grants-2013_03
Patent number
US08404866B2

Reaction notes

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