Tetrahydrofuran → HCID 21474801, compound

HRID 1901744Notes

Reaction equation

HRID 1901744 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][CH2:6][CH:7]1[O:11][C:10](=[O:12])[N:9]([CH:13]([CH:18]([CH3:20])[CH3:19])[C:14](OC)=[O:15])[CH2:8]1.[BH4-].[Li+].O1CCCC1>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[O:5][CH2:6][CH:7]1[O:11][C:10](=[O:12])[N:9]([CH:13]([CH:18]([CH3:19])[CH3:20])[CH2:14][OH:15])[CH2:8]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 21474780HCID 21474780, compound

Product 1

HCID 21474801HCID 21474801, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A procedure similar to that described in Preparation 5 was repeated, except that 1.14 g of methyl 2-[5-(3-chlorophenoxymethyl)-2-oxooxazolidin-3-yl]-3-methylbutanoate (less polar isomer), obtained as described in Preparation 99, 144 mg of lithium borohydride, 12 ml of anhydrous tetrahydrofuran and 105 mg of anhydrous methanol were used, to give 1.02 g of the title compound having an Rf value of 0.26 (on silica gel thin layer chromatography, using a 1:1 mixture of ethyl acetate and hexane as the developing solvent) from the less polar diastereomer.

Workup

  1. customA procedure similar to that described in Preparation 5
  2. customobtained

Sources & evidence

ORD record
ord-349ea931f2bf4fab98106542151bed83
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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