Lithium hydroxide, monohydrate → 2-Amino-2-(6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl)propane-1,3-diol

HRID 1921688Notes

Reaction equation

HRID 1921688 reaction equation
[OH:1][CH2:2][C:3]([NH:24]C(=O)C)([CH2:22][OH:23])[CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:10]=2)[CH2:5]1.O[Li].O>CO.C1COCC1.O.C(OCC)(=O)C>[NH2:24][C:3]([CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[CH:10]=2)[CH2:5]1)([CH2:22][OH:23])[CH2:2][OH:1]

Participants

7

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57577382N-[1,3-Dihydroxy-2-(6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl)propan-2-yl]acetamide

Product 1

HCID 575773772-Amino-2-(6-octyl-1,2,3,4-tetrahydronaphthalen-2-yl)propane-1,3-diolYield 75%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of compound 7 (53 mg, 0.14 mmol) and LiOH.H2O (45 mg, 1.1 mmol) in MeOH (3 ml), THF (1.5 ml) and water (3 ml) was stirred at 50° C. for 5 hours and diluted with ethyl acetate (20 ml). The solution was washed with brine (2×10 mL) and dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography (Silica gel, 50% MeOH in CH2Cl2) to provide 35 mg of compound VPC104061(75%).

Workup

  1. washThe solution was washed with brine (2×10 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was purified by column chromatography (Silica gel, 50% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-41f908304bdf4c4cb6df0c3216223a91
Source dataset
uspto-grants-2012_05
Patent number
US08173710B2

Reaction notes

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