3-Pentanol → HCID 11441321, compound

HRID 1020390Notes

Reaction equation

HRID 1020390 reaction equation
[C:1]([N:4]1[C@@H:10]2[C@H:5]1[C@@H:6]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:7][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9]2)(=[O:3])[CH3:2].[CH3:24][CH2:25][CH:26]([OH:29])[CH2:27][CH3:28]>C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Cu+2]>[C:1]([NH:4][C@@H:5]1[C@@H:6]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:7][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:9][C@H:10]1[O:29][CH:26]([CH2:27][CH3:28])[CH2:25][CH3:24])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 114283-PentanolHCID 11594989ethyl (1S,5S,6R)-7-acetyl-5-((tert-butoxycarbonyl)amino)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate

Product 1

HCID 11441321HCID 11441321, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 2734996copper(II) trifluoromethanesulfonateCatalyst

Procedure

To a solution of aziridine 13 (16 mg; 0.05 mmol) in 3-pentanol (1 mL) was added Cu(OTf)2 (3 mg; 0.008 mmol). After 16 h the reaction mixture was quenched by addition of saturated solution of NaHCO3 (0.1 ml) and concentrated. Chromatography of residue [hexane-ethyl acetate (3:1)→(2:1), 4.5 ml silica] afforded 12 mg (60%) of compound 15 as white solid: m.p.=144-145° C. (CHCl3); RF=0.3 (ethyl acetate-hexane 1:2); [α]20D=−21.54 (c=0.5, CHCl3); IR (KBr, cm−1) ν 3324, 2976, 3966, 2933, 2877, 2855, 1720, 1687, 1658, 1587, 1536, 1459, 1384, 1297, 1250, 1176, 1146, 1130, 1086, 1054, 1019, 948; 1H NMR (CDCl3, 600 Mhz) δ 6.81 (s, 1H), 5.80 (d, J=9.6 Hz, 1H), 5.11 (d, J=9.0 Hz, 1H), 4.22 (m, 2H), 4.08 (ddd, J=2 x≈4.8, 9.3 Hz, 1H), 3.97 (m, 1H), 3.81 (ddd, J=5.1, 2×9.6 Hz, 1H), 3.37 (qui, J=5.7 Hz, 1H), 2.76 (dd, J=4.8, 17.7 Hz, 1H), 2.31 (m, 1H), 2.00 (s, 3H), 1.51 (m, 4H), 1.44 (s, 9H), 1.30 (t, J=7.2 Hz, 3H), 0.90 (m, 6H); 13C NMR (CDCl3, 150 Mhz) δ 170.85, 165.98, 156.35, 137.65, 129.34, 82.21, 79.73, 76.00, 61.00, 54.47, 49.00, 31.01, 28.33, 26.12, 25.69, 23.41, 14.20, 9.54, 9.21.

Workup

  1. customAfter 16 h the reaction mixture was quenched by addition of saturated solution of NaHCO3 (0.1 ml)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-3a08570d96e840baad1281dae14c1f0d
Source dataset
uspto-grants-2014_05
Patent number
US08716333B2

Reaction notes

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