Methanol → HCID 90956681, compound

HRID 2183859Notes

Reaction equation

HRID 2183859 reaction equation
[C:1]([OH:6])(=[O:5])C(O)=O.[NH2:7][CH2:8][CH2:9][C@@H:10]([O:14][C:15]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:16]=1[C:17]#[N:18])[CH2:11][O:12]C.[BH4-].[Li+].CO>O1CCCC1>[Cl:23][C:21]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([CH:22]=1)[O:14][C@@H:10]([CH2:11][OH:12])[CH2:9][CH2:8][NH:7][C:1](=[O:5])[O:6][C:16]([CH3:19])([CH3:17])[CH3:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 69743753HCID 69743753, compound

Product 1

HCID 90956681HCID 90956681, compoundYield 148.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The product from step (c) (881 mg, 2.39 mmol) was dissolved in anhydrous tetrahydrofuran (20 ml) and lithium borohydride (2M solution in tetrahydrofuran, 2.6 ml, 5.26 mmol) added dropwise. The mixture was stirred at room temperature for 18 h. Methanol (5 ml) was added and the reaction stirred for 15 minutes. The solvent was removed in vacuo and the residue chromatographed on flash silica, eluting with hexane:ethyl acetate (3:2, then 1:1) to give the title compound as a colourless oil (605 mg, 74%).

Workup

  1. stirringthe reaction stirred for 15 minutes
  2. customThe solvent was removed in vacuo
  3. customthe residue chromatographed on flash silica
  4. washeluting with hexane:ethyl acetate (3:2

Sources & evidence

ORD record
ord-53c021cb441e4782add3f4d98eeff7bc
Source dataset
uspto-grants-2005_05
Patent number
US06900243B2

Reaction notes

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