Sodium cyanoborohydride → HCID 21241934, compound

HRID 1761575Notes

Reaction equation

HRID 1761575 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH:5]([C:7]1[NH:8][CH:9]=[CH:10][CH:11]=1)O.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[CH2:5][C:7]1[NH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 21241926HCID 21241926, compound

Product 1

HCID 21241934HCID 21241934, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
-5 °C

Procedure

A 2-(3'-amino-α-hydroxybenzyl)pyrrole is dissolved in an inert organic solvent (such as a lower alkanol, preferably methanol), cooled to about -20° to 10° C., preferably -5° C., and treated with a molar excess of a reducing agent (such as sodium cyanoborohydride in glacial acetic acid). The reaction mixture is allowed to warm to about ambient temperature and is stirred for a period of about 0.5 to 36 hours, preferably 1 to 18 hours, and most preferably about 2 hours. The reaction is then quenched (e.g., with saturated sodium carbonate) and extracted with ethyl acetate. The extract is washed with water, dried and evaporated in vacuo, and then purified, e.g., by column chromatography over slica gel, to obtain the 2-(3'-aminobenzyl)pyrrole of Formula 11.

Workup

  1. temperatureto warm to about ambient temperature
  2. custommost preferably about 2 hours
  3. customThe reaction is then quenched (e.g., with saturated sodium carbonate)
  4. extractionextracted with ethyl acetate
  5. washThe extract is washed with water
  6. customdried
  7. customevaporated in vacuo
  8. custompurified

Sources & evidence

ORD record
ord-4330e1b832ce4fefa1e9fd733e41f5d7
Source dataset
uspto-grants-1989_05
Patent number
US04826869

Reaction notes

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