Sodium Hydroxide → HCID 178501038, compound

HRID 1670676Notes

Reaction equation

HRID 1670676 reaction equation
[OH-:1].[Na+].Br[CH:4]([CH3:23])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)=[O:6]>O.CN(C=O)C>[C:5]([C:7]1[CH:12]=[CH:11][C:10]([C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)(=[O:6])[CH:4]([CH3:23])[OH:1]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178501036HCID 178501036, compound

Product 1

HCID 178501038HCID 178501038, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydroxide (370 mg, 9.25 mmol) in water (2 mL) was added to a stirred solution of methyl trans-4-[4-(2-bromopropanoyl)phenyl]cyclohexanecarboxylate (prepared as described in Patent Application WO2004/047755) (3.264 g, 9.25 mmol) in DMF (10 mL). The mixture was stirred for 40 minutes then extracted with ether (5×20 mL). The extracts were combined, dried and concentrated. The crude product was purified by flash column chromatography eluting with 20-40% EtOAc/hexanes to give the title compound (1.76 g, 66%) as a solid; 1H NMR δ 7.94 (2H, d), 7.39 (2H, d), 5.29 (1H, d), 5.08-4.98 (1H, m), 3.62 (3H, s), 2.68-2.54 (1H, m), 2.48-2.35 (1H, m), 2.08-1.94 (2H, m), 1.90-1.79 (2H, m), 1.60-1.40 (4H, m), 1.28 (3H, s); MS 313 (M+Na)+.

Workup

  1. extractionthen extracted with ether (5×20 mL)
  2. customdried
  3. concentrationconcentrated
  4. customThe crude product was purified by flash column chromatography
  5. washeluting with 20-40% EtOAc/hexanes

Sources & evidence

ORD record
ord-470bbd64c893400f8187859e85f6c856
Source dataset
uspto-grants-2011_08
Patent number
US07994179B2

Reaction notes

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