Lithium borohydride → 2-{[3-(2-Hydroxy-ethyl)-benzylamino]-methyl}-phenol

HRID 553316Notes

Reaction equation

HRID 553316 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[OH:20])[CH:6]=1.[BH4-].[Li+]>O1CCCC1>[OH:2][CH2:3][CH2:4][C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[CH2:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67165213{3-[(2-Hydroxy-benzylamino)-methyl]-phenyl}-acetic acid methyl ester

Product 1

HCID 671645402-{[3-(2-Hydroxy-ethyl)-benzylamino]-methyl}-phenolYield 54.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of {3-[(2-hydroxy-benzylamino)-methyl]-phenyl}-acetic acid methyl ester (0.81 g) in anhydrous tetrahydrofuran (20 mL) was treated with lithium borohydride (186 mg) and the whole stirred at room temperature for 30 minutes. The reaction mixture was then heated at 60° C. for 2 hours under nitrogen. After cooling to room temperature the mixture was partitioned between diethyl ether and dilute aqueous hydrochloric acid, the aqueous layer was separated and treated with excess solid sodium bicarbonate. The aqueous layer was extracted three times with dichloromethane and the combined organic washings were dried, filtered and evaporated under reduced pressure to yield the sub-titled compound (400 mg).

Workup

  1. temperatureThe reaction mixture was then heated at 60° C. for 2 hours under nitrogen
  2. temperatureAfter cooling to room temperature the mixture
  3. customwas partitioned between diethyl ether and dilute aqueous hydrochloric acid
  4. customthe aqueous layer was separated
  5. additiontreated with excess solid sodium bicarbonate
  6. extractionThe aqueous layer was extracted three times with dichloromethane
  7. customthe combined organic washings were dried
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4b547477048846b29bd18b2faeef9ebe
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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