1-Isocyanato-4-methoxybenzene → HCID 131733266, compound

HRID 510490Notes

Reaction equation

HRID 510490 reaction equation
CCN(C(C)C)C(C)C.Cl.[C@H:11]12[N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@H:15]([CH2:16][CH2:17]1)[CH2:14][NH:13][CH2:12]2.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]=[C:35]=[O:36])=[CH:30][CH:29]=1>C(Cl)Cl>[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([N:13]2[CH2:14][C@@H:15]3[N:18]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H:11]([CH2:17][CH2:16]3)[CH2:12]2)=[O:36])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 794431-Isocyanato-4-methoxybenzeneHCID 81531DiisopropylethylamineHCID 56777171HCID 56777171, compound

Product 1

HCID 131733266HCID 131733266, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (0.53 mL, 3.0 mmol) was added to a suspension of tert-butyl (1S,5R)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate hydrochloride (0.50 g, 2.00 mmol) in DCM (20 mL). To the mixture was added 4-methoxyphenyl isocyanate (0.26 mL, 2.0 mmol) dropwise, and the reaction mixture was stirred for 20 h. The reaction mixture was washed with brine (2×20 mL), then passed through a phase separator and evaporated. The crude material was purified by flash chromatography on silica, with a gradient of 25% increasing to 75% EtOAc/isohexane over 20 column volumes. The title compound (0.74 g, >99%) was obtained as a white solid. LCMS (ES+) 362.8 (M+H)+, RT 2.02 minutes (method 3).

Workup

  1. washThe reaction mixture was washed with brine (2×20 mL)
  2. customevaporated
  3. customThe crude material was purified by flash chromatography on silica, with a gradient of 25%
  4. temperatureincreasing to 75% EtOAc/isohexane over 20 column volumes

Sources & evidence

ORD record
ord-55ef7eb64e7149029b7342db267ab39f
Source dataset
uspto-grants-2015_08
Patent number
US09096614B2

Reaction notes

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