Hydrochloric Acid → HCID 10205646, compound

HRID 857349Notes

Reaction equation

HRID 857349 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:16]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]([F:24])=[CH:13][C:12]=3[N:11]3[CH2:25][CH2:26][CH:27]([CH2:28][C:29]([OH:31])=[O:30])[C:10]=23)=[CH:4][CH:3]=1.[BH4-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:16]([CH:18]([OH:23])[C:19]([F:21])([F:22])[F:20])=[CH:15][C:14]([F:24])=[CH:13][C:12]=3[N:11]3[CH2:25][CH2:26][CH:27]([CH2:28][C:29]([OH:31])=[O:30])[C:10]=23)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 10183781HCID 10183781, compound

Product 1

HCID 10205646HCID 10205646, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (+/−)-[9-[(4-chlorophenyl)sulfanyl]-6-fluoro-8-(trifluoroacetyl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetic acid (Example 11, 78 mg) in MeOH (5 mL) at r.t. was added 50 mg of NaBH4. The reaction mixture was stirred at r.t. for 3 hours and 1N HCl was slowly added The aqueous layer was extracted with EtOAc and the combined organic layers were dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with EtOAc/Hexanes/AcOH (20:30:1) to provide 60 mg of the title compound as a white solid.

Workup

  1. extractionwas extracted with EtOAc
  2. dry with materialthe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluted with EtOAc/Hexanes/AcOH (20:30:1)

Sources & evidence

ORD record
ord-ef5c108ca31b4865b1a2f0f0e0950830
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

Loading…