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Sodium borohydride → (3-Chloro-4-{1-hydroxy-3-oxo-4,9-bis[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetic acid

HRID 913169
Notes
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Reaction equation

HRID 913169 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:35][C:36]([OH:38])=[O:37])[CH:5]=[CH:6][C:7]=1[N:8]1[C:16](=[O:17])[C:15]2[C:14]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[C:13]3[CH:24]=[CH:25][CH:26]=[CH:27][C:12]3=[C:11]([O:28][CH2:29][C:30]([F:33])([F:32])[F:31])[C:10]=2[C:9]1=[O:34].[BH4-].[Na+]>C(O)C.O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:35][C:36]([OH:38])=[O:37])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:16]([OH:17])[C:15]2[C:14]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[C:13]3[CH:24]=[CH:25][CH:26]=[CH:27][C:12]3=[C:11]([O:28][CH2:29][C:30]([F:32])([F:33])[F:31])[C:10]=2[C:9]1=[O:34]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 4311764Sodium borohydride2×HCID 24760115(3-Chloro-4-{1,3-dioxo-4,9-bis[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetic acid

Product 1

HCID 58012477(3-Chloro-4-{1-hydroxy-3-oxo-4,9-bis[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetic acidYield 93.3%

Reagents, catalysts & solvents 2

HCID 702Ethanol
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-chloro-4-{1,3-dioxo-4,9-bis[(2,2,2-trifluoroethyl)oxy]-1,3-dihydro-2H-benzo[f]isoindol-2-yl}phenyl)acetic acid (0.250 g, 0.45 mmol) in ethanol (10 ml) and tetrahydrofuran (20 ml), was added sodium borohydride (0.059 g, 1.56 mmol) in portions. A further addition of sodium borohydride (0.059 g, 1.56 mmol) was made and stirring continued for 10 minutes. The mixture was evaporated and then quenched with aqueous saturated ammonium chloride solution until the mixture was pH 7. This was extracted ×2 with ethyl acetate, washed with brine, dried over magnesium sulphate and evaporated to give the crude product (0.235 g, 0.42 mmol). LC/MS: Rt=3.28, [MH]+564.

Workup

  1. customThe mixture was evaporated
  2. customquenched with aqueous saturated ammonium chloride solution until the mixture
  3. extractionThis was extracted ×2 with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-54f9ac94019544a1bea83e4321104b0b
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08026270B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes