Diethyl Ether → HCID 67959873, compound

HRID 1529414Notes

Reaction equation

HRID 1529414 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.C([O:15][C:16](=O)[CH:17]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH3:28])[N:23]=[C:22]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)[CH3:18])(C)C>C1COCC1>[OH:15][CH2:16][CH:17]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([CH3:28])[N:23]=[C:22]2[C:29]1[N:34]=[C:33]([O:35][C@H:36]2[CH2:43][N:42]([C:44]([O:46][C:47]([CH3:48])([CH3:50])[CH3:49])=[O:45])[CH2:41][CH2:40][C:37]32[CH2:38][CH2:39]3)[CH:32]=[N:31][CH:30]=1)[CH3:18]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21226445Aluminium lithium hydrideHCID 67958463HCID 67958463, compound

Product 1

HCID 67959873HCID 67959873, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride, 1.0 M solution in Et2O (109 μl, 0.109 mmol) was added to a solution of (4R)-tert-butyl 4-((6-(5-(1-isopropoxy-1-oxopropan-2-yl)-1-methyl-1H-indazol-3-yl)pyrazin-2-yl)oxy)-6-azaspiro[2.5]octane-6-carboxylate (30 mg, 0.055 mmol) in THF (546 μl) at 0° C. for 1 h. The reaction was quenched with EtOAc and triturated with NH4Cl before it was filtered and concentrated to give (4R)-tert-butyl 4-((6-(5-(1-hydroxypropan-2-yl)-1-methyl-1H-indazol-3-yl)pyrazin-2-yl)oxy)-6-azaspiro[2.5]octane-6-carboxylate (18 mg, 0.036 mmol, 66.8% yield) as a yellow oil. MS (ESI, pos. ion) m/z: 494.0 (M+1).

Workup

  1. customThe reaction was quenched with EtOAc
  2. customtriturated with NH4Cl before it
  3. filtrationwas filtered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2a019f9545db4a76a6aef7637180022e
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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