Aluminium lithium hydride → HCID 67959804, compound

HRID 1529411Notes

Reaction equation

HRID 1529411 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:11][C:12](=O)[CH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[N:18]=[C:17]2[C:29]1[N:34]=[C:33]([O:35][C@H:36]2[CH2:43][N:42]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:41][CH2:40][C:37]32[CH2:39][CH2:38]3)[CH:32]=[N:31][CH:30]=1)(C)(C)C>C1COCC1>[OH:11][CH2:12][CH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[N:18]=[C:17]2[C:29]1[N:34]=[C:33]([O:35][C@H:36]2[CH2:43][N:42]([C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:41][CH2:40][C:37]32[CH2:39][CH2:38]3)[CH:32]=[N:31][CH:30]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67960475HCID 67960475, compound

Product 1

HCID 67959804HCID 67959804, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Lithium aluminum hydride in THF (181 μL, 0.181 mmol) was added to a solution of (4R)-tert-butyl 4-(6-(5-(2-tert-butoxy-2-oxoethyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrazin-2-yloxy)-6-azaspiro[2.5]octane-6-carboxylate (56 mg, 0.090 mmol) in THF (904 μL) at 0° C.; the reaction was stirred for 1 h. The crude was quenched with EtOAc and was adsorbed onto silica and was purified via automated flash chromatography (silica gel) with 100% hexanes to 40% EtOAc/hexanes to give (4R)-tert-butyl 4-(6-(5-(2-hydroxyethyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrazin-2-yloxy)-6-azaspiro[2.5]octane-6-carboxylate as a pale yellow oil. MS (ESI, pos. ion) m/z: 550.2 (M+1).

Workup

  1. customThe crude was quenched with EtOAc
  2. customwas purified

Sources & evidence

ORD record
ord-8908db7136a1423aa4059db888c185c3
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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