Hydrochloric Acid → (3S)-3-(4-bromophenyl)cyclopentanol

HRID 1443411Notes

Reaction equation

HRID 1443411 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][CH2:11][C:10](=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+].Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9357Potassium Sodium TartrateHCID 21225700DiisobutylaluminumhydrideHCID 49833221(R)-3-(4-Bromophenyl)cyclopentan-1-one

Product 1

HCID 68666346(3S)-3-(4-bromophenyl)cyclopentanolYield 100.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of (3R)-3-(4-Bromophenyl)cyclopentanone (1.14 g, 4.77 mmol, CARBOXYLIC ACID 4, Step A) in 10 mL of CH2Cl2 at −78° C. was added diisobutylaluminum hydride (7.2 mL, 1.0 M in CH2Cl2). The mixture was stirred at −78° C. for 1 hr and then 5.0 mL of sat'd Rochelle's salt aqueous solution was added. The mixture was poured into diluted HCl solution and extracted with CH2Cl2 (3×10 mL). Organic layers were combined, washed with sat'd NaHCO3 and brine. The organic layer was dried over MgSO4 and concentrated to give 1.16 g (100%) of the title compound as a 1:1 ratio diastereomeric mixture, which cannot be separated by chromatography.

Workup

  1. extractionextracted with CH2Cl2 (3×10 mL)
  2. washwashed with sat'd NaHCO3 and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-80bc0f6c1c5140ca91e9d2a092905181
Source dataset
uspto-grants-2010_02
Patent number
US07659294B2

Reaction notes

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