Methyl Isocyanate → 1-(SR)-(3,5-Bis(trifluoromethyl)phenyl)methoxy-2-(SR)-phenyl-3-(RS)-(N-(methylaminocarbonyl)-N-methylamino)cyclopentane

HRID 1289948Notes

Reaction equation

HRID 1289948 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][CH:15]2[CH2:19][CH2:18][CH:17]([NH:20][CH3:21])[CH:16]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CCN(C(C)C)C(C)C.[CH3:39][N:40]=[C:41]=[O:42]>C(Cl)Cl>[F:1][C:2]([F:28])([F:29])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][CH:15]2[CH2:19][CH2:18][CH:17]([N:20]([C:41]([NH:40][CH3:39])=[O:42])[CH3:21])[CH:16]2[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 81531DiisopropylethylamineHCID 75024269HCID 75024269, compound

Product 1

HCID 883499701-(SR)-(3,5-Bis(trifluoromethyl)phenyl)methoxy-2-(SR)-phenyl-3-(RS)-(N-(methylaminocarbonyl)-N-methylamino)cyclopentaneYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 25 mg of amine prepared in Example 11 and 0.05 mL of DIPEA in 0.5 mL of methylene chloride was added 15 mg of methyl isocyanate. After 1.5 h in a sealed vial, the volatiles were evaporated under a stream of nitrogen and the residue was purified on a 1 mm preparative silica gel plate eluted with ethyl acetate to afford 25 mg of title compound. Mass spec (NH3 /CI): 475 (M+1).

Workup

  1. customAfter 1.5 h in a sealed vial, the volatiles were evaporated under a stream of nitrogen
  2. customthe residue was purified on a 1 mm preparative silica gel plate
  3. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-4ee5f931854f446a97fa77d3cde079cb
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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