HCID 56926626, compound → HCID 53495647, compound

HRID 1042970Notes

Reaction equation

HRID 1042970 reaction equation
[CH3:1][O:2][C:3](=[O:27])/[C:4](/[NH:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[CH:5]/[C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H][H]>CO>[CH3:1][O:2][C:3](=[O:27])[C@@H:4]([NH:18][C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:5][C:6]1[CH2:10][CH2:9][CH2:8][C:7]=1[O:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 56926626HCID 56926626, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53495647HCID 53495647, compoundYield 101.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 2-L autoclave, a slurry of compound (V) (n=1, R=Ph, R1=PhO, R2=Me) (100 g, 0.27 mol) in methanol (900 mL) was charged and bubbled with nitrogen for 30 minutes. Then [Rh(COD)(ScRp-DuanPhos)]BF4 (135 mg, 0.2 mmol) was added under nitrogen. The autoclave was then charged hydrogen to 10 bar and stirred at room temperature overnight. The reaction was monitored with HPLC. After the reaction completed, pressure of the hydrogenator was released, and the solution was concentrated to provide the product as oil (100 g). The ee was >99% which was determined by HPLC using Chiralpak AD-H column.

Workup

  1. custombubbled with nitrogen for 30 minutes
  2. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-f059c68783444ff49ad1e75c87bfa8fc
Source dataset
uspto-grants-2013_10
Patent number
US08558023B2

Reaction notes

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