Sodium borohydride → HCID 20318590, compound

HRID 866782Notes

Reaction equation

HRID 866782 reaction equation
[CH2:1]([N:8]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:9][C:10]([C:12]1[CH:20]=[C:16]([C:17]([NH2:19])=[O:18])[C:15]([O:21][CH3:22])=[CH:14][CH:13]=1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[CH2:23]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][CH:10]([C:12]1[CH:20]=[C:16]([C:17]([NH2:19])=[O:18])[C:15]([O:21][CH3:22])=[CH:14][CH:13]=1)[OH:11])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 203185845-(N,N-dibenzylglycyl)-o-anisamide

Product 1

HCID 20318590HCID 20318590, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-(N,N-dibenzylglycyl)-o-anisamide (13.0g) in ethanol (800ml) was treated with excess solid sodium borohydride (ca.2g) and allowed to stand overnight at room temperature. The ethanol was then evaporated under reduced pressure and the residue partitioned between ethyl acetate and water. The ethyl acetate was separated, washed with brine, dried over MgSO4 and evaporated. The residue readily crystallised on trituration with ether to afford 5-(2-dibenzylamino-1-hydroxyethyl)-o-anisamide as a white solid (11.1g) m.p. 120°-123°.

Workup

  1. customThe ethanol was then evaporated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe ethyl acetate was separated
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue readily crystallised on trituration with ether

Sources & evidence

ORD record
ord-0464a336d0c84de59eb1894c4ad7e640
Source dataset
uspto-grants-1978_07
Patent number
US04101579

Reaction notes

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