Aluminium lithium hydride → 7-(1-Methyl-pyrrolidin-3-ylmethoxy)-4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinoline

HRID 8276

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O[C:15]([N:17]1[CH2:21][CH2:20][CH:19]([CH2:22][O:23][C:24]2[CH:33]=[C:32]3[C:27]([C:28]([C:34]4[C:38]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=5)=[N:37][N:36]5[CH2:45][CH2:46][CH2:47][C:35]=45)=[CH:29][CH:30]=[N:31]3)=[CH:26][CH:25]=2)[CH2:18]1)=O)C1C=CC=CC=1>O1CCCC1.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>[CH3:15][N:17]1[CH2:21][CH2:20][CH:19]([CH2:22][O:23][C:24]2[CH:33]=[C:32]3[C:27]([C:28]([C:34]4[C:38]([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=5)=[N:37][N:36]5[CH2:45][CH2:46][CH2:47][C:35]=45)=[CH:29][CH:30]=[N:31]3)=[CH:26][CH:25]=2)[CH2:18]1

Participants

Conditions

Temperature: 65 °C

Procedure

To a 1 M solution of lithium aluminum hydride in tetrahydrofuran (0.60 mL, 0.59 mmol) is added a solution of 3-[4-(2-pyridin-2-yl-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-quinolin-7-yloxymethyl]-pyrrolidine-1-carboxylic acid benzyl ester (215 mg, 0.39 mmol) in tetrahydrofuran (2 mL). The mixture is heated at 65° C. for 2 h, cooled to 0° C., and diluted with saturated aqueous sodium potassium tartrate solution. The mixture is extracted with chloroform and the organic portion chromatographed on SiO2 to yield the title compound, 112 mg (67%), as a yellow foam.

Workup

temperaturecooled to 0° C.
extractionThe mixture is extracted with chloroform
customthe organic portion chromatographed on SiO2

Sources & evidence

ORD record: ord-4c71d311966240d38a6e88fb07d5d068
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07087626B2

Linked notes

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