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Water → 1-[2,4-Bis(trifluoromethyl)benzyl]-5-(hydroxymethyl)azepan-2-one

HRID 1620634
Notes
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Reaction equation

HRID 1620634 reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:4]=1[CH2:5][N:6]1[C:12](=[O:13])[CH2:11][CH2:10][CH:9]([C:14](OCC)=[O:15])[CH2:8][CH2:7]1.[BH4-].[Li+].O>C1COCC1>[F:28][C:2]([F:1])([F:27])[C:3]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:4]=1[CH2:5][N:6]1[CH2:7][CH2:8][CH:9]([CH2:14][OH:15])[CH2:10][CH2:11][C:12]1=[O:13]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 86678800Ethyl 1-[2,4-bis(trifluoromethyl)benzyl]-7-oxoazepane-4-carboxylate

Product 1

HCID 866788011-[2,4-Bis(trifluoromethyl)benzyl]-5-(hydroxymethyl)azepan-2-oneYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 1-[2,4-bis(trifluoromethyl)benzyl]-7-oxoazepane-4-carboxylate (14.8 g) in THF (400 mL) was added lithium borohydride (4.5 g). The reaction mixture was stirred at 50° C. for 1 hr, water was added, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (12.0 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-395a40ceaad646bfaf3a6e47f2fc35d9
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772277B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes