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Water → HCID 178519364, compound

HRID 521058
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Reaction equation

HRID 521058 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[CH:35]=[CH:34][C:14]2[C@@H:15]3[C@H:20]([CH2:21][CH2:22][C:13]=2[CH:12]=1)[N:19]([C:23]([C:25]1[CH:33]=[CH:32][C:28]2[NH:29][CH:30]=[N:31][C:27]=2[CH:26]=1)=[O:24])[CH2:18][CH2:17][CH2:16]3)=O.O>O1CCCC1>[NH:29]1[C:28]2[CH:32]=[CH:33][C:25]([C:23]([N:19]3[C@@H:20]4[C@@H:15]([C:14]5[CH:34]=[CH:35][C:11]([CH2:9][OH:8])=[CH:12][C:13]=5[CH2:22][CH2:21]4)[CH2:16][CH2:17][CH2:18]3)=[O:24])=[CH:26][C:27]=2[N:31]=[CH:30]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178497109HCID 178497109, compound

Product 1

HCID 178519364HCID 178519364, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

Lithium aluminum hydride (1 mol/L in tetrahydrofuran, 0.5 mL) is added to a solution of cis-4-(1H-benzoimidazole-5-carbonyl)-1,2,3,4,4a,5,6,10b-octahydro-benzo[f]quinoline-8-carboxylic acid methyl ester (150 mg) in tetrahydrofuran (6 mL) cooled to −10° C. The resulting solution is stirred for 2 h while warming to ca. −3° C. in the cooling bath. Little water is added carefully and the resulting mixture is filtered over Celite. The filtrate is diluted with ethyl acetate and dried (MgSO4). The solvent is evaporated and the residue is triturated with ethyl acetate and dried to give the title compound as a solid. Yield: 56 mg (40% of theory); LC (method 1): tR=2.03 min; Mass spectrum (ESI+): m/z=362 [M+H]+.

Workup

  1. temperaturewhile warming to ca. −3° C. in the cooling bath
  2. filtrationthe resulting mixture is filtered over Celite
  3. additionThe filtrate is diluted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customThe solvent is evaporated
  6. customthe residue is triturated with ethyl acetate
  7. customdried

Sources & evidence

ORD record
ord-99d5f058cbbe4a40824aedf0a78d5a2a
Source dataset
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09328072B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes