Hydrochloric Acid → HCID 86610004, compound

HRID 1176401Notes

Reaction equation

HRID 1176401 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Cl:11][C:12]1[N:17]=[C:16]([CH3:18])[N:15]=[C:14]([O:19][CH2:20][CH2:21][O:22][CH:23]2[CH:28]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=4[O:47][CH3:48])=[CH:31][CH:30]=3)[CH2:27][CH2:26][N:25]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:24]2)[C:13]=1[CH2:56][C:57](OC)=[O:58].CO.Cl>O1CCCC1>[Cl:11][C:12]1[N:17]=[C:16]([CH3:18])[N:15]=[C:14]([O:19][CH2:20][CH2:21][O:22][CH:23]2[CH:28]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH2:36][CH2:37][CH2:38][O:39][CH2:40][C:41]4[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=4[O:47][CH3:48])=[CH:33][CH:34]=3)[CH2:27][CH2:26][N:25]([C:49]([O:51][C:52]([CH3:55])([CH3:53])[CH3:54])=[O:50])[CH2:24]2)[C:13]=1[CH2:56][CH2:57][OH:58]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21225700DiisobutylaluminumhydrideHCID 86610005HCID 86610005, compound

Product 1

HCID 86610004HCID 86610004, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

4.8 ml of diisobutylaluminium hydride (1.5M in toluene) are added dropwise at −70° C. over 10 minutes to the solution of 1.74 g of tert-butyl 3-[2-(6-chloro-5-methoxycarbonylmethyl-2-methylpyrimidin-4-yloxy)ethoxy]-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate in 20 ml of tetrahydrofuran. The reaction mixture is warmed slowly to −40° C. over 3 hours, admixed with 0.4 ml of methanol and subsequently warmed to room temperature. The reaction solution is admixed with 20 ml of 0.5N HCl and stirred vigorously over 10 minutes. The reaction mixture is extracted with tert-butyl methyl ether (2×). The combined organic phases are washed successively with 1M sodium potassium tartrate solution and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.35 (2:1 EtOAc-heptane); Rt=5.75.

Workup

  1. temperaturesubsequently warmed to room temperature
  2. extractionThe reaction mixture is extracted with tert-butyl methyl ether (2×)
  3. washThe combined organic phases are washed successively with 1M sodium potassium tartrate solution and brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1f154aaa4a1e4e198f0490efcadf678f
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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