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Water → 4-Chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-quinoline-6-methanol

HRID 540287
Notes
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Reaction equation

HRID 540287 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18](OC)=[O:19])[CH:16]=2)[N:11]=[C:10]([N:22]2[CH2:28][C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[S:25](=[O:34])(=[O:33])[CH2:24][CH2:23]2)[CH:9]=1.O>O1CCCC1>[Cl:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH2:18][OH:19])[CH:16]=2)[N:11]=[C:10]([N:22]2[CH2:28][C:27]3[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=3[S:25](=[O:34])(=[O:33])[CH2:24][CH2:23]2)[CH:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 71255132methyl 4-chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinoline-6-carboxylate

Product 1

HCID 712544654-Chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)-quinoline-6-methanolYield 86%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

To a slurry of lithium aluminum hydride (46 mg, 1.21 mmol) in tetrahydrofuran (5 mL) was added a solution of methyl 4-chloro-2-(1,1-dioxido-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)quinoline-6-carboxylate (400 mg, 0.96 mmol) in tetrahydrofuran (10 mL) at 0° C. under a nitrogen atmosphere. After being allowed to warm to room temperature and stirred for 2 hours, the reaction mixture was cooled to 0° C. and treated with water (0.2 mL) to quench the reaction. The resulting mixture was stirred for 30 minutes, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford 321 mg of the desired product as a white solid (yield was 86%).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. customto quench
  3. customthe reaction
  4. stirringThe resulting mixture was stirred for 30 minutes
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5d272716eafb4777b319ebeedc9116d6
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08871756B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes