Tetrahydrofuran → HCID 21474816, compound

HRID 1901743Notes

Reaction equation

HRID 1901743 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[O:5][CH2:6][CH:7]1[O:11][C:10](=[O:12])[N:9]([CH:13]([CH2:19][CH2:20][CH3:21])[C:14](OCC)=[O:15])[CH2:8]1.O1CCCC1.[BH4-].[Li+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[O:5][CH2:6][CH:7]1[O:11][C:10](=[O:12])[N:9]([CH:13]([CH2:19][CH2:20][CH3:21])[CH2:14][OH:15])[CH2:8]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 21474704HCID 21474704, compound

Product 1

HCID 21474816HCID 21474816, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A procedure similar to that described in Preparation 5 was repeated, except that 4.31 g of ethyl 2-[5-(3-chlorophenoxymethyl)-2-oxooxazolidin-3-yl]pentanoate (polar isomer), obtained as described in Preparation 96, 40 ml of anhydrous tetrahydrofuran, 0.42 g of lithium borohydride and 0.31 g of anhydrous methanol were used, to give 2.03 g of the title compound, melting at 98° C. to 102° C., from the polar diastereomer.

Workup

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

Sources & evidence

ORD record
ord-2250ca0785a94f63a6b0f73e249dcb1a
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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