Lithium borohydride → HCID 67166025, compound

HRID 553298Notes

Reaction equation

HRID 553298 reaction equation
[BH4-].[Li+].C[O:4][C:5](=O)[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([CH2:15][N:16]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[F:25])[CH:8]=1>O1CCCC1>[C:29]([O:28][C:26](=[O:27])[N:16]([CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[F:25])[CH2:15][C:9]1[CH:8]=[C:7]([CH2:6][CH2:5][OH:4])[CH:12]=[CH:11][C:10]=1[O:13][CH3:14])([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 67165718HCID 67165718, compound

Product 1

HCID 67166025HCID 67166025, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2M Lithium borohydride in tetrahydrofuran (1.5 mL) was added to a solution of [3-({tert-butoxycarbonyl-[2-(2-fluoro-phenyl)-ethyl]-amino}-methyl)-4-methoxy-phenyl]-acetic acid methyl ester (0.25 g) in tetrahydrofuran (5 mL), at 0° C. under nitrogen. After 4 hours, the reaction was quenched by the addition of ethyl acetate. The reaction was diluted with ethyl acetate and extracted sequentially twice with saturated aqueous sodium bicarbonate solution, brine, dried (magnesium sulfate) and evaporated. Purification on silica, eluting with a gradient of methanol (0% to 1%) in dichloromethane, to give the subtitle compound as an oil (0.25 g).

Workup

  1. customthe reaction was quenched by the addition of ethyl acetate
  2. additionThe reaction was diluted with ethyl acetate
  3. extractionextracted sequentially twice with saturated aqueous sodium bicarbonate solution, brine
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated
  6. customPurification on silica
  7. washeluting with a gradient of methanol (0% to 1%) in dichloromethane

Sources & evidence

ORD record
ord-0f863be4898d4f2281a062c541aa4243
Source dataset
uspto-grants-2011_05
Patent number
US07951954B2

Reaction notes

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