Hydrochloric Acid → HCID 57941410, compound

HRID 1437885Notes

Reaction equation

HRID 1437885 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].C[O:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:21](=[O:22])[C:20]3[C@@H:19]4[C:23]([CH3:25])([CH3:24])[C@@:16]([CH3:26])([CH2:17][CH2:18]4)[C:15]=3[NH:14]2)=[CH:9][CH:8]=1.O.Cl>C(S)C>[OH:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[C:21](=[O:22])[C:20]3[C@@H:19]4[C:23]([CH3:25])([CH3:24])[C@@:16]([CH3:26])([CH2:17][CH2:18]4)[C:15]=3[NH:14]2)=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6451240Aluminum(III) ChlorideHCID 57941426HCID 57941426, compound2×

Product 1

HCID 57941410HCID 57941410, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6343EthanethiolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of aluminum chloride (2.40 g, 18.0 mmol) in ethanethiol (20 mL) was cooled to 0° C. and (4S,7R)-2-(4-methoxy-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 40; 2.00 g, 6.7 mmol) was added. The flask was capped and the reaction mixture was stirred at 0° C. for about 20 min and then at room temperature for 2 h. The solution was added to water (100 mL) with vigorous stirring and the resulting mixture was acidified to pH 1-2 with 1 M HCl. The resulting solid was filtered off, washed with water and then hexanes, air-dried and then dried under vacuum to give (4S,7R)-2-(4-hydroxy-phenyl)-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (1.63 g, 85%) as an off-white solid.

Workup

  1. customThe flask was capped
  2. waitat room temperature for 2 h
  3. stirringwith vigorous stirring
  4. filtrationThe resulting solid was filtered off
  5. washwashed with water
  6. dry with materialhexanes, air-dried
  7. customdried under vacuum

Sources & evidence

ORD record
ord-b47c77b3b45346daaab85393e173c471
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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