Sodium Hydroxide → HCID 57941327, compound

HRID 1438088Notes

Reaction equation

HRID 1438088 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][N:11]1[C:19](=[O:20])[C:18]2[C@@H:17]3[C:21]([CH3:23])([CH3:22])[C@@:14]([CH3:24])([CH2:15][CH2:16]3)[C:13]=2[N:12]1[CH3:25].[OH-].[Na+]>O1CCCC1.CO>[CH3:25][N:12]1[C:13]2[C@@:14]3([CH3:24])[C:21]([CH3:22])([CH3:23])[C@H:17]([CH2:16][CH2:15]3)[C:18]=2[C:19](=[O:20])[N:11]1[CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:26])=[O:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57941519HCID 57941519, compound

Product 1

HCID 57941327HCID 57941327, compoundYield 64.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-((4S,7R)-1,7,8,8-tetramethyl-3-oxo-1,3,4,5,6,7-hexahydro-4,7-methano-indazol-2-ylmethyl)-benzoic acid methyl ester (304 mg, 0.86 mmol) and 1 M NaOH (1.5 mL, 1.5 mmol) in tetrahydrofuran (2.4 mL) and methanol (1.2 mL) was stirred overnight at room temperature. The reaction mixture was partitioned between water (100 mL) and ether (100 mL). The aqueous layer was acidified to pH<3 with 1 M HCl and the resulting mixture was extracted with chloroform (100 mL) and then chloroform containing a small amount of methanol (100 mL). The combined organic extracts were dried (magnesium sulfate), filtered, evaporated, and dried under vacuum to give 2-((4S,7R)-1,7,8,8-tetramethyl-3-oxo-1,3,4,5,6,7-hexahydro-4,7-methano-indazol-2-ylmethyl)-benzoic acid (188 mg, 64%) as an off-white solid).

Workup

  1. customThe reaction mixture was partitioned between water (100 mL) and ether (100 mL)
  2. extractionthe resulting mixture was extracted with chloroform (100 mL)
  3. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  4. filtrationfiltered
  5. customevaporated
  6. customdried under vacuum

Sources & evidence

ORD record
ord-f0d88890427a49db9ba06a6155a4f5b7
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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