Butyl isocyanate → HCID 59536326, compound

HRID 445348Notes

Reaction equation

HRID 445348 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][CH2:11][NH:10]2)=[CH:5][CH:4]=1.[CH2:21]([N:25]=[C:26]=[O:27])[CH2:22][CH2:23][CH3:24]>C(Cl)Cl>[CH2:21]([NH:25][C:26]([N:10]1[CH2:11][CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:9]1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:19])[F:20])=[CH:8][CH:7]=1)=[O:27])[CH2:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 8110Butyl isocyanateHCID 28293305(R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 59536326HCID 59536326, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline (198 mg, 714 μmol, Example 87, Step 3) in DCM (2.0 mL) was added n-butyl isocyanate (88 μL, 785 μmol). The resulting mixture was then stirred at RT for overnight. Then, the solvent was removed and the residue was mixed with silica gel. The solid mixture was the purified by silica gel flash column chromatography using ISCO instrument (solid loading, 0%-400% EtOAc/hexane) to give the title compound as a colorless solid. MS (ESI, positive ion) m/z: 377 (M+H).

Workup

  1. customThen, the solvent was removed
  2. additionthe residue was mixed with silica gel
  3. custompurified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-5db235c1bca04ff5b5de2a0b7f82cc16
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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