Hydrochloric Acid → HCID 86701156, compound

HRID 1396668Notes

Reaction equation

HRID 1396668 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH2:10][CH:9]1[C:18](O)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>O1CCCC1>[Cl:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:9]([CH2:18][OH:19])[CH2:10]2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86701157HCID 86701157, compound

Product 1

HCID 86701156HCID 86701156, compoundYield 105.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1.17 g of 1-(tert-butoxycarbonyl)-5-chloro-2,3-dihydro-1H-indole-2-carboxylic acid and 23 mL of tetrahydrofuran was added dropwise 15.7 mL of a 1 M solution of a borane-tetrahydrofuran complex in tetrahydrofuran under ice-cooling, followed by warming to room temperature and stirring overnight. After ice-cooling again, 15 mL of 1 M hydrochloric acid was added dropwise thereto, followed by extraction with chloroform. The obtained organic layer was washed with water, a saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 1.18 g of tert-butyl 5-chloro-2-(hydroxymethyl)-2,3-dihydro-1H-indole-1-carboxylate as a pale yellow solid.

Workup

  1. temperaturecooling
  2. temperatureAfter ice-cooling again
  3. extractionfollowed by extraction with chloroform
  4. washThe obtained organic layer was washed with water
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-19f8b44f5e69491ca042bcad1d105fd4
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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