Methanol → HCID 86618886, compound

HRID 252409Notes

Reaction equation

HRID 252409 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:15][CH:16]([CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[C:24]([O:31][CH2:32][CH2:33][O:34][CH3:35])[CH:25]=[CH:26][CH:27]=2)[CH:22]=1)[CH:17]([CH3:19])[CH3:18])[C:10](OCC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].CO>O1CCCC1>[OH:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH2:15][CH:16]([CH2:20][C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[C:24]([O:31][CH2:32][CH2:33][O:34][CH3:35])[CH:25]=[CH:26][CH:27]=2)[CH:22]=1)[CH:17]([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 66889244HCID 66889244, compound

Product 1

HCID 86618886HCID 86618886, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.44 g of ethyl 2-tert-butoxycarbonylamino-4-[8-(2-methoxyethoxy)naphthalen-2-ylmethyl]-5-methylhexanoate in 35 ml of tetrahydrofuran is admixed at room temperature with 0.25 g of lithium borohydride in portions. After 23 hours, 35 ml of methanol are added dropwise and the resulting mixture is concentrated by evaporation at 40° C. The residue is once more admixed with 35 ml of methanol and again concentrated by evaporation to dryness. The residue is admixed with ice/1N HCl and extracted with dichloromethane (3×)—the combined organic phases are washed with water, dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F).

Workup

  1. concentrationthe resulting mixture is concentrated by evaporation at 40° C
  2. concentrationagain concentrated by evaporation to dryness
  3. extractionextracted with dichloromethane (3×)—the combined organic phases
  4. washare washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-5d681454cb4e4716843c41525c5d3cd5
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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