Lithium borohydride → HCID 67165345, compound

HRID 553300Notes

Reaction equation

HRID 553300 reaction equation
[BH4-].[Li+].C([O:5][C:6](=O)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH2:15][N:16]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:18][O:19][CH3:20])[CH:9]=1)C>O1CCCC1.C(OCC)(=O)C>[C:24]([O:23][C:21](=[O:22])[N:16]([CH2:15][CH2:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH2:7][CH2:6][OH:5])[CH:9]=1)[CH2:17][CH2:18][O:19][CH3:20])([CH3:25])([CH3:27])[CH3:26]

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 67165067HCID 67165067, compound

Product 1

HCID 67165345HCID 67165345, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2M Lithium borohydride in tetrahydrofuran solution (0.7 mL) was added to a solution of (3-{2-[tert-butoxycarbonyl-(2-methoxy-ethyl)-amino]-ethyl}-phenyl)-acetic acid ethyl ester (230 mg) in tetrahydrofuran (10 mL) and heated to reflux for 1 hour. On cooling, the reaction was diluted with ethyl acetate and extracted sequentially, twice with saturated aqueous sodium bicarbonate solution, once with brine, dried over magnesium sulfate and evaporated, to give the subtitle compound as an oil (200 mg).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. temperatureOn cooling
  4. extractionextracted sequentially, twice with saturated aqueous sodium bicarbonate solution, once with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-dccd4f2e67164b45b317150cc93af36b
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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