Isopropanol → (trans)-N-[[2-[3-(Methylethoxy)phenyl]cyclopropyl]methyl] butanamide

HRID 1291715Notes

Reaction equation

HRID 1291715 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[CH2:10][C@H:9]2[CH2:11][NH:12][C:13](=[O:17])[CH2:14][CH2:15][CH3:16])[CH:5]=[CH:6][CH:7]=1.[C:18]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:23]=CC=C[CH:19]=1.C(O)(C)C.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCOCC>[CH3:19][CH:18]([O:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[CH2:10][C@H:9]2[CH2:11][NH:12][C:13](=[O:17])[CH2:14][CH2:15][CH3:16])[CH:5]=[CH:6][CH:7]=1)[CH3:23]

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 70274674(trans)-N-[[2-(3-Hydroxyphenyl)cyclopropyl]methyl]butanamide

Product 1

HCID 15860314(trans)-N-[[2-[3-(Methylethoxy)phenyl]cyclopropyl]methyl] butanamideYield 31%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a rapidly stirred solution of (trans)-N-[[2-(3-hydroxyphenyl)cyclopropyl]methyl] butanamide (390 mg, 1.7 mmol), triphenylphosphine (498 mg, 1.9 mmol) and isopropanol (150 mg, 2.5 mmol) in THF (10 mL) at 0° C. was added diethyl azodicarboxylate (331 mg, 1.9 mmol) in one portion. After stirring for 2 h, the suspension was diluted with Et2O (100 mL), washed with H2O, 2N NaOH, and brine, dried (K2CO3) and concentrated to a give a crude wax. The resulting material was purified by chromatography (silica gel, 35% EtOAc/hexane) to afford 144 mg (31%) of the title compound: 1H NMR (300 MHz, CDCl3) δ0.85-0.94 (m, 5H), 1.22-1.24 (m, 1H), 1.29 (d, J=6.7 Hz, 6H), 1.58-1.68 (m, 2H), 1.70-1.77 (m, 1H), 2.14 (t, J=6.0 Hz, 2H), 3.14-3.36 (m, 2H), 4.44-4.54 (m, 1H), 5.81 (br s, 1H), 6.53-6.67 (m, 3H), 7.13 (t, J=7.2 Hz, 1H); IR (NaCl Film) 3294, 2974, 1644, 1610, 1550, 1492 cm-1 ; MS m/e 275; Analysis calc'd for C17H25 NO2 : C, 74.14; H, 9.15; N, 5.09; found: C, 73.77; H, 8.99; N, 4.82.

Workup

  1. washwashed with H2O, 2N NaOH, and brine
  2. dry with materialdried (K2CO3)
  3. concentrationconcentrated to
  4. customa give a crude wax
  5. customThe resulting material was purified by chromatography (silica gel, 35% EtOAc/hexane)

Sources & evidence

ORD record
ord-c15fd363a82948029331a9326e293cb5
Source dataset
uspto-grants-1998_05
Patent number
US05753709

Reaction notes

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