2-(Benzenesulfonyl)-3-phenyloxaziridine → (+/-)-3-Benzyl-2-(1-hydroxy-propyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one

HRID 1795944Notes

Reaction equation

[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][N:11]2[N:10]=[C:9]1[CH2:18][CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:38])C=CC=CC=1>C1COCC1>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][N:11]2[N:10]=[C:9]1[CH:18]([OH:38])[CH2:19][CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 3-benzyl-2-propyl-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (2.0 g, 7.48 mmol) in THF (45 mL) at −78° C. was added KHMDS (0.5 M in toluene, 17.2 mL, 8.6 mmol) dropwise. After stirring at −78° C. for 10 min, the orange solution was charged with a solution of racemic 2-benzenesulfonyl-3-phenyloxaziridine (2.15 g, 8.23 mmol) in THF (5 mL). The pale yellow solution was stirred at −78° C. for 25 min and was then quenched with 50 mL of saturated NaHCO3 solution. The mixture was extracted with EtOAc (3×50 mL) and the pooled organic extracts were dried over anhydrous MgSO4 and concentrated in vacuo. Purification of the crude product by flash column chromatography (SiO2, EtOAc/Hexane 1:4) gave the title compound as a colorless viscous oil which solidified upon standing (1.40 g, 66%): 1H NMR (CDCl3) δ 7.25 (m, 5H), 7.12 (t, 1H, J=1.4 Hz), 7.01 (m, 1H), 6.49 (m, 1H), 5.34 (d, 1H, J=16.1 Hz), 5.18 (d, 1H, J=16.2 Hz), 4.45 (m, 1H), 2.55 (brs, 1H), 1.78 (m, 1H), 1.63 (m, 1H), 0.88 (t, 3H, J=7.36 Hz); 13C NMR (CDCl3) δ 155.4, 150.7, 136.7, 129.4, 128.2, 126.7, 121.4, 118.5, 111.5, 109.6, 71.0, 44.8, 29.8, 10.3; MS (ESI+) 284.17 (M++H).

Workup

stirringThe pale yellow solution was stirred at −78° C. for 25 min
customwas then quenched with 50 mL of saturated NaHCO3 solution
extractionThe mixture was extracted with EtOAc (3×50 mL)
dry with materialthe pooled organic extracts were dried over anhydrous MgSO4
concentrationconcentrated in vacuo
customPurification of the crude product by flash column chromatography (SiO2, EtOAc/Hexane 1:4)

Sources & evidence

ORD record: ord-38517cff9dc54f08a6b2dfd26e8f87da
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030118B2

Reaction notes

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