HCID 22645937, compound → HCID 9837356, compound

HRID 2414460Notes

Reaction equation

HRID 2414460 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][CH:4]([CH2:12][NH:13][C:14](=[O:16])[CH3:15])[CH2:3]1.[H][H]>C1(C)C=CC=CC=1>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C@@H:4]([CH2:12][NH:13][C:14](=[O:16])[CH3:15])[CH2:3]1

Participants

4

Reactant 2

HCID 22645937HCID 22645937, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9837356HCID 9837356, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

35.1 g of N-(4-oxochroman-2-ylmethyl)acetamide are suspended in 90 ml of toluene, and 1.6 ml of a 10 millimolar solution consisting of [Rh((S)-ToIBINAP)(COD)Cl] in toluene, are added under inert conditions. This suspension is hydrogenated in an autoclave at 100 bar of hydrogen and 100° C. After 12 hours, enantiomerically pure (>99% ee) (R)-N-(4-oxochroman-2-ylmethyl)acetamide is crystallised by cooling to room temperature. Drying gives 31.04 g of (R)-N-(4-oxochroman-2-ylmethyl)acetamide.

Workup

  1. additionare added under inert conditions
  2. customenantiomerically pure (>99% ee) (R)-N-(4-oxochroman-2-ylmethyl)acetamide is crystallised
  3. customDrying

Sources & evidence

ORD record
ord-452fec8faf71410b9d294fecc7fa189d
Source dataset
uspto-grants-2004_11
Patent number
US06812353B2

Reaction notes

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