m-Chloroperbenzoic acid → HCID 23507881, compound

HRID 381609Notes

Reaction equation

HRID 381609 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:16]2[C:25]3[CH2:24][CH2:23][CH:22]=[CH:21][C:20]=3[CH:19]=[CH:18][CH:17]=2)[C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])=[CH:5][CH:4]=1)#[N:2].ClC1C=C(C=CC=1)C(OO)=[O:31]>C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[CH2:24][CH2:23][CH:22]2[O:31][CH:21]23)[C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 23507935HCID 23507935, compound

Product 1

HCID 23507881HCID 23507881, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of a 3:1 mixture of N-(4-cyanophenyl)-N-(7,8-dihydro-1-naphthyl)-2,2,2-trifluoro acetamide and the corresponding 5,6-dihydro isomer (4.3 g, 13 mmol) and m-chloroperoxybenzoic acid (80-85%, 4.0 g, 19 mmol) (Aldrich) in methylene chloride (60 ml) was stirred for 50 minutes at room temperature. The solution was diluted with methylene chloride (100 ml), washed with saturated NaHCO3 solution (2×30 ml), dried (K2CO3), and concentrated in vacuo. The epoxide isomers were separated by chromatography on silica gel eluting with diethyl ether:hexane (7:13 to 9:11) and recrystallization of the enriched isomer from diethyl ether:hexane. The mother liqour was combined with some mixed fractions from the chromatography and purified by repeating the procedure. The combined solid was dried under high vacuum to give N-(4-cyanophenyl)-2,2,2-trifluoro-N-(1a,2,3,7b-tetrahydronaphth[1,2-b]oxiren-4-yl)acetamide (2.8 g). 1H NMR (CDCl3, 200 MHz) δ: 1.69 (dt, J=14,5 Hz, 1H, CH2), 2.03-2.25 (m, 1H, CH2), 2.31-2.69 (m, 2H, CH2), 3.70-3.78 (m, 1H, OCH), 3.90 (d, J=4 Hz, 1H, OCH), 7.29-7.42 (m, 4H, Ar), 7.50-7.60 (m, 1H, Ar), 7.63 (d, J=9 Hz, 2H, Ar). Anal. Calculated for C19H13F3N2O2: C, 63.69; H, 3.66; N, 7.82. Found: C, 63.70; H, 3.66; N, 7.76.

Workup

  1. washwashed with saturated NaHCO3 solution (2×30 ml)
  2. dry with materialdried (K2CO3)
  3. concentrationconcentrated in vacuo
  4. customThe epoxide isomers were separated by chromatography on silica gel eluting with diethyl ether:hexane (7:13 to 9:11) and recrystallization of the enriched isomer from diethyl ether
  5. custompurified
  6. customThe combined solid was dried under high vacuum

Sources & evidence

ORD record
ord-8b4d05f6db99421b8197f55c9f044279
Source dataset
uspto-grants-2001_10
Patent number
US06306865B1

Reaction notes

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