Lithium borohydride → HCID 59577304, compound

HRID 2041996Notes

Reaction equation

HRID 2041996 reaction equation
[C:1]([C:5]1[CH:36]=[CH:35][CH:34]=[CH:33][C:6]=1[O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:32])[CH:15]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:16](OCC2C=CC=CC=2)=[O:17])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>>[C:1]([C:5]1[CH:36]=[CH:35][CH:34]=[CH:33][C:6]=1[O:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:32])[CH:15]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:16][OH:17])[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 4148881Lithium borohydrideHCID 59577252HCID 59577252, compound

Product 1

HCID 59577304HCID 59577304, compoundYield 24.7%

Procedure

Benzyl 3-[4-(2-tert-butylphenoxy)piperidin-1-yl]-3-oxo-2-phenylpropanoate (167 mg, 0.34 mmol) obtained in Example 174 and lithium tetrahydroborate (2.0M, THF solution, 0.41 mL, 0.82 mmol) were stirred at room temperature for 3 days. The reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride, and the ethyl acetate layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 75:25-25:75) to give the title compound (32 mg, 24%) as a colorless oil.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride
  2. dry with materialthe ethyl acetate layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate 75:25-25:75)

Sources & evidence

ORD record
ord-bf603a0fdd0e48d78f23abfd899e2143
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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