HCID 20694322, compound → HCID 20694318, compound

HRID 380503Notes

Reaction equation

HRID 380503 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[C@H:10]([C:18](N2[C@@H](CC3C=CC=CC=3)COC2=O)=[O:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[C@H:10]([CH2:18][OH:19])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 20694322HCID 20694322, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20694318HCID 20694318, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5.84 g (13.1 mmol) of (S)-N-[(1-Benzyl)-4-(R)-(3-thienyl)-3-(S)-pyrrolidinylcarbonyl]-4-benzyl-2-oxazolidinone (Step 2) in 60 mL of THF at 0° C. was added 15.7 mL (15.7 mmol) of a solution of LiAlH4 (1.0 M in ether). The solution was stirred at room temperature for 3 h, then was quenched by addition of 5N NaOH solution. The mixture was diluted with ether and the organic fraction was washed twice with 5N NaOH solution. The combined organic fractions were dried over Na2SO4, filtered, and the filtrate concentrated. The residue was purified by chromatography (silica, acetone:hexanes, 1:6) to afford 3.22 g of the title compound. 1H NMR (CDCl3) δ7.33-7.34 (m, 4H), 7.26-7.30 (m, 2H), 7.02-7.04 (m, 2H), 3.77 (d of d, 1H, J=10.3, 4.3 Hz), 3.68 (d of d, 1H, J=10.1, 5.0 Hz); Mass spectrum (ESI) m/e=274 (M+1); [α]D=−13.6 (c.=1.60, CHCl3).

Workup

  1. customwas quenched by addition of 5N NaOH solution
  2. additionThe mixture was diluted with ether
  3. washthe organic fraction was washed twice with 5N NaOH solution
  4. dry with materialThe combined organic fractions were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated
  7. customThe residue was purified by chromatography (silica, acetone:hexanes, 1:6)

Sources & evidence

ORD record
ord-435d59b67e3847a081d97e2165611325
Source dataset
uspto-grants-2001_10
Patent number
US06303593B1

Reaction notes

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