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HCID 68704917, compound → Cyclopenta[c][1]benzopyran-8-ol, 2,2-difluoro-1,2,3,3a,4,9b-hexahydro-4-(4-hydroxyphenyl)-, (3aS,4R,9bR)-

HRID 1176825
Notes
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Reaction equation

HRID 1176825 reaction equation
[F:1][C:2]1([F:29])[CH2:28][CH:5]2[CH:6]([C:18]3[CH:23]=[CH:22][C:21]([O:24]COC)=[CH:20][CH:19]=3)[O:7][C:8]3[CH:9]=[CH:10][C:11]([O:14]COC)=[CH:12][C:13]=3[CH:4]2[CH2:3]1>C1COCC1.Cl.CCOC(C)=O>[F:29][C:2]1([F:1])[CH2:28][C@@H:5]2[C@H:6]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[O:7][C:8]3[CH:9]=[CH:10][C:11]([OH:14])=[CH:12][C:13]=3[C@@H:4]2[CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 68704917HCID 68704917, compound

Product 1

HCID 11197931Cyclopenta[c][1]benzopyran-8-ol, 2,2-difluoro-1,2,3,3a,4,9b-hexahydro-4-(4-hydroxyphenyl)-, (3aS,4R,9bR)-Yield 100%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857
Ethyl Acetate
Solvent

Procedure

Stir a solution of difluorocyclopentane 29 (196 mg, 0.480 mmol) in 7 mL of THF and 3 mL of 3 M HCl overnight. Add 1 mL of 5 M HCl and let stir overnight. Dilute the solution with EtOAc. Separate the aqueous solution and extract 2× with EtOAc. The combined organic solutions were washed with saturated aqueous sodium bicarbonate, brine, dried over Na2SO4, filtered, and concentrated. Absorb to 2 g of silica gel and purify by silica gel chromatography (10 g silica gel, 10 to 60% EtOAc/Hexanes over 30 min at 35 mL/min) to give 155 mg (0.48 mmol, 100%) of difluorocyclopentane 30. The enantiomers were separated by preparative chiral chromatography (Chiralpak AD, 65/35 heptane/ethanol).

Workup

  1. customSeparate the aqueous solution
  2. extractionextract 2× with EtOAc
  3. washThe combined organic solutions were washed with saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customAbsorb to 2 g of silica gel
  8. custompurify by silica gel chromatography (10 g silica gel, 10 to 60% EtOAc/Hexanes over 30 min at 35 mL/min)

Sources & evidence

ORD record
ord-00f8ac3cf0814c718449837d4036512e
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07842822B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes