Sodium Hydroxide → HCID 68666307, compound

HRID 1443413Notes

Reaction equation

HRID 1443413 reaction equation
C([O:4][C@@H:5]1[CH2:9][CH2:8][C@@H:7]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)[CH2:6]1)(=O)C.[OH-].[Na+]>CCO>[Br:16][C:13]1[CH:12]=[CH:11][C:10]([C@@H:7]2[CH2:8][CH2:9][C@@H:5]([OH:4])[CH2:6]2)=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68666334HCID 68666334, compound

Product 1

HCID 68666307HCID 68666307, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (1R,3R)-3-(4-bromophenyl)cyclopentyl acetate (CARBOXYLIC ACID 8, Step B, 536 mg, 1.9 mmol) in 5.0 mL of EtOH was added sodium hydroxide (1.9 mL, 5.0 N). After stirring at rt for 30 min, solvent was removed and the residue was partitioned between sat'd NaHCO3 (50 mL) and CH2Cl2 (50 mL). The aqueous layer was separated and extracted with CH2Cl2 (2×50 mL). Organic layers were combined, dried over MgSO4, and concentrated. Chromatography on a Biotage 40+M cartridge using 7:3 v/v hexanes/EtOAc as the eluant afforded 445 mg (97%) of the title compound: 1H NMR δ 1.49 (br. s, 1H), 1.56-1.81 (m, 2H), 2.05-2.27 (m, 4H), 3.35 (m, 1H), 4.52 (m, 1H), 7.09 (d, J=8.2, 2H), 7.40 (d, J=8.3, 2H).

Workup

  1. customsolvent was removed
  2. customthe residue was partitioned between sat'd NaHCO3 (50 mL) and CH2Cl2 (50 mL)
  3. customThe aqueous layer was separated
  4. extractionextracted with CH2Cl2 (2×50 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-565fe6b0b81c4a478104488b4bcc41cf
Source dataset
uspto-grants-2010_02
Patent number
US07659294B2

Reaction notes

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