Hydrochloric Acid → HCID 14936170, compound

HRID 1862475Notes

Reaction equation

HRID 1862475 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH:14]2[CH:15]=[CH:16][CH:11]1[C:12]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[CH:13]2)=[O:9])([CH3:6])([CH3:5])[CH3:4].Cl>C(O)C.C1COCC1.O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C>[C:3]([O:7][C:8]([N:10]1[CH:14]2[CH2:15][CH2:16][CH:11]1[C:12]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)(=[O:18])=[O:19])=[CH:13]2)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 14936167tert-Butyl 2-(4-methylbenzene-1-sulfonyl)-7-azabicyclo[2.2.1]hepta-2,5-diene-7-carboxylate

Product 1

HCID 14936170HCID 14936170, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 62601Nickel acetate tetrahydrateCatalystHCID 702EthanolSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of nickel (II) acetate tetrahydrate (161 g, 647 mmol) in ethanol (400 mL) was added dropwise a solution of sodium borohydride (24.6 g, 1.54 mol) in ethanol (500 mL). This mixture was cooled to 0° C. and a solution of 7-tert-Butoxycarbonyl-2-p-tolylsulfonyl-7-azabicyclo[2.2.1]-hepta-2,5-diene (44.49 g, 128 mmol) in THF (300 mL) was added. Concentrated HCl (100 mL) was next added and the mixture allowed to stir overnight. After quenching the reaction with sodium bicarbonate, the mixture was filtered over a celite pad and extracted several times with ethyl acetate. The combined organic layers were dried with sodium sulfate, concentrated, then purified by flash chromatography with 4:1 hexane:ethyl acetate to give 7-tert-Butoxycarbonyl-2-p-tolylsulfonyl-7-azabicyclo[2.2.1]-hepta-2-ene (32.57 g, 73%) as a colorless solid.

Workup

  1. customAfter quenching
  2. customthe reaction with sodium bicarbonate
  3. filtrationthe mixture was filtered over a celite pad
  4. extractionextracted several times with ethyl acetate
  5. dry with materialThe combined organic layers were dried with sodium sulfate
  6. concentrationconcentrated
  7. custompurified by flash chromatography with 4:1 hexane

Sources & evidence

ORD record
ord-e8aaf8bb2557405d80c5668f5b8ab247
Source dataset
uspto-grants-2003_03
Patent number
US06538010B1

Reaction notes

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