Borane → HCID 19003077, compound

HRID 1613467Notes

Reaction equation

HRID 1613467 reaction equation
[CH:1]1([N:4]=[C:5]2[C:9]3[N:10]([CH3:18])[C:11]4[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][C:16]=4[C:8]=3[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.B.FC(F)(F)C(O)=O>C1COCC1>[CH:1]1([NH:4][CH:5]2[CH:9]3[N:10]([CH3:18])[C:11]4[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][C:16]=4[CH:8]3[CH2:7][CH2:6]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6331BoraneHCID 6422Trifluoroacetic acidHCID 15288859HCID 15288859, compound

Product 1

HCID 19003077HCID 19003077, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-Cyclopropylimino-4-methyl-1,2,3,4-tetrahydrocyclopent[b]indol-7-ol (8.7 g) was placed in a 3-neck flask and cooled to 0° C. in an ice-water bath. A 1M solution of borane in THF (540 ml) was added in a dropwise manner. The mixture was stirred for 1 hour while it was slowly warmed to room temperature. The mixture was cooled back down to 0° C. and trifluoroacetic acid (119 ml) was added in a dropwise manner. The solution was stirred for 15 minutes and THF was removed in vacuo. The mixture was neutralized with 10% NaOH solution, extracted with methylene chloride (4×500 ml), dried (Na2SO4) and concentrated to give 3-(N-cyclopropyl)amino-1,2,3,3a,4,8b-hexahydro-4-methylcyclopent[b]indol-7-ol (8.8 g).

Workup

  1. temperaturewas slowly warmed to room temperature
  2. additionwas added in a dropwise manner
  3. stirringThe solution was stirred for 15 minutes
  4. customTHF was removed in vacuo
  5. extractionextracted with methylene chloride (4×500 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-edf500f9a510486fa2cc04b1f106c1e8
Source dataset
uspto-grants-1993_03
Patent number
US05192789

Reaction notes

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