Hydrochloric Acid → HCID 18794915, compound

HRID 1004335Notes

Reaction equation

HRID 1004335 reaction equation
[OH:1][CH:2]([CH3:26])[CH:3]([CH2:11][C:12]1[O:13][C:14]([C:17](=[O:25])[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:16]=1)[C:4](OC(C)(C)C)=[O:5].[BH4-].[Li+].Cl>O1CCCC1>[OH:5][CH2:4][CH:3]([CH2:11][C:12]1[O:13][C:14]([C:17](=[O:25])[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:16]=1)[CH:2]([OH:1])[CH3:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 86755322tert-butyl (2RS,3SR)-3-hydroxy-2-{5-(phenylcarbamoyl)-2-furylmethyl}butanoate

Product 1

HCID 18794915HCID 18794915, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3.0 g of tert-butyl (2RS,3SR)-3-hydroxy-2-{5-(phenylcarbamoyl)-2-furylmethyl}butanoate [the compound prepared in Reference Example 3(2)] in 30 ml of tetrahydrofuran was stirred together with 1.09 g of lithium borohydride at room temperature for 2 hours. The reaction solution was cooled to 0° C., mixed with 2N hydrochloric acid and extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure to give 1.56 g of the title compound as a colorless oily substance.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThe desiccant was filtered off
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-94a7efa76333450daf13f63ed25224ae
Source dataset
uspto-grants-2000_04
Patent number
US06048894

Reaction notes

Loading…