Sodium cyanoborohydride → HCID 58386466, compound

HRID 74523Notes

Reaction equation

HRID 74523 reaction equation
C([BH3-])#N.[Na+].[N:5]1([CH2:10][CH2:11][CH2:12][C:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH:14]=2)[CH2:9][CH2:8][CH2:7][CH2:6]1>C(O)(=O)C>[N:5]1([CH2:10][CH2:11][CH2:12][CH:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][CH2:14]2)[CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydride2×HCID 583865083-(3-pyrrolidin-1-yl-propyl)-1H-indole

Product 1

HCID 58386466HCID 58386466, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

At 15° C. 508 mg (8.10 mmol) sodium cyanoborohydride was added to 600 mg (2.63 mmol) 3-(3-pyrrolidin-1-yl-propyl)-1H-indole in 7.50 g acetic acid and the mixture was stirred for 1 h at 15° C. After this time another 600 mg sodium cyanoborohydride were added and the mixture was stirred at 15° C. for 3 h. The reaction mixture was evaporated down using the rotary evaporator and combined with 40 mL of a 4M hydrochloric acid solution. The reaction mixture was stirred for 1h at RT. Then the mixture was made basic with potassium carbonate and extracted with ethyl acetate (2×50 mL). The combined organic phases were dried and evaporated down i. vac. The product was reacted further without any further purification.

Workup

  1. customAt 15° C
  2. stirringthe mixture was stirred at 15° C. for 3 h
  3. customThe reaction mixture was evaporated down
  4. customthe rotary evaporator
  5. stirringThe reaction mixture was stirred for 1h at RT
  6. extractionextracted with ethyl acetate (2×50 mL)
  7. customThe combined organic phases were dried
  8. customevaporated down i
  9. customThe product was reacted further without any further purification

Sources & evidence

ORD record
ord-a878730b334c4115b5d4b0b5490ed774
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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