Lithium borohydride → N-[1,3-Dihydroxy-2-(6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl)propan-2-yl]acetamide

HRID 1921687Notes

Reaction equation

HRID 1921687 reaction equation
[BH4-].[Li+].C([O:5][C:6](=O)[C:7]([NH:31][C:32](=[O:34])[CH3:33])([CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:19]=2)[CH2:14]1)[C:8](OCC)=[O:9])C>C1COCC1.C(OCC)(=O)C>[OH:9][CH2:8][C:7]([NH:31][C:32](=[O:34])[CH3:33])([CH2:6][OH:5])[CH:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:19]=2)[CH2:14]1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 57577378Diethyl acetamido(6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl)propanedioate

Product 1

HCID 57577382N-[1,3-Dihydroxy-2-(6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl)propan-2-yl]acetamideYield 33%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Lithium borohydride (2M solution in THF, 0.88 ml, 1.76 mmol) was added to compound 6 (200 mg, 0.44 mmol) in 5 ml THF at 0° C. The reaction mixture was stirred at room temperature for 48 hours and diluted with 40 ml ethyl acetate. The solution was washed with brine (2×20 mL) and dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography (Silica gel, 4% MeOH in CH2Cl2) to provide 55 of mg compound 7 (33%).

Workup

  1. washThe solution was washed with brine (2×20 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by column chromatography (Silica gel, 4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-03f214d8cbb544d98c3f5607c87e6bc1
Source dataset
uspto-grants-2012_05
Patent number
US08173710B2

Reaction notes

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