HCID 131732502, compound → HCID 123869053, compound

HRID 1854558Notes

Reaction equation

HRID 1854558 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2/[CH:20]=[CH:21]/[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C@H:12]([CH3:27])[N:11]1[C:28](=[O:38])[CH2:29][C:30]1[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=1[Cl:37])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[B-](F)(F)(F)F.CC(C)P([C]1[CH][CH][CH][CH]1)C(C)C.CC(C)P([C]1[CH][CH][CH][CH]1)C(C)C.C1CC=CCCC=C1.[Fe].[Rh]>[Si:1]([O:8][CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C@H:12]([CH3:27])[N:11]1[C:28](=[O:38])[CH2:29][C:30]1[C:31]([Cl:37])=[CH:32][CH:33]=[CH:34][C:35]=1[Cl:36])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 131732502HCID 131732502, compound

Product 1

HCID 123869053HCID 123869053, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 178420242HCID 178420242, compoundCatalystHCID 887MethanolSolvent

Procedure

In the dry box to a 85 ml Parr autoclave with stir bar and glass liner, add 1,1′-bis(di-i-propylphosphino)ferrocene(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate (7 mg, 0.010 mmol). Add ethyl (2E)-3-{(1S,3R)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-[(2,6-dichlorophenyl)acetyl]-1-methyl-1,2,3,4-tetrahydroisoquinolin-5-yl}prop-2-enoate (133 mg, 0.23 mmol) as a solution in anhydrous methanol (5 mL). Seal the autoclave and remove from the dry box. Purge the vessel with hydrogen and pressurize to 690 kPa of hydrogen. Stir at room temperature overnight. Vent and open the vessel. Concentrate the reaction mixture under reduced pressure. Purify the residue by silica gel chromatography, eluting with 25% methyl t-butyl ether:hexanes to give the title compound as a clear colorless oil (121 mg, 0.21 mmol). MS (m/z): 578 (M+1).

Workup

  1. customSeal the autoclave
  2. customremove from the dry box
  3. customPurge the vessel with hydrogen
  4. stirringStir at room temperature overnight
  5. concentrationConcentrate the reaction mixture under reduced pressure
  6. customPurify the residue by silica gel chromatography
  7. washeluting with 25% methyl t-butyl ether

Sources & evidence

ORD record
ord-147a242da73945d68f500383f4b7999d
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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