tert-butyl-1-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)ethylcarbamate → tert-butyl 1-((2S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-2-yl)ethylcarbamate

HRID 556167Notes

Reaction equation

HRID 556167 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][CH:8]([C:10]1[CH2:19][C@@H:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[Cl:27][C:22]1[CH:21]=[C:20]([C@H:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH2:11][C@@H:10]([CH:8]([NH:7][C:6](=[O:28])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH3:9])[CH2:19]2)[CH:25]=[CH:24][C:23]=1[Cl:26]

Participants

4

Reactant 1

HCID 66808903tert-butyl-1-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)ethylcarbamate

Product 1

HCID 58950748tert-butyl 1-((2S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-2-yl)ethylcarbamateYield 61.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl-1-((S)-4-(3,4-dichlorophenyl)-3,4-dihydronaphthalen-2-yl)ethylcarbamate 49b (Example 21.3) (60 mg, 0.14 mmol) in ethyl acetate (6 mL) was added palladium on charcoal (30 mg, 5%). The mixture was then stirred under hydrogen (1 atm) for 1 h. The catalyst was removed through a pad of Celite. The filtrate was concentrated. Chiral AD column separation (ethanol/methanol/hexane/DEA=3:2:95:0.1) afforded tert-butyl 1-((2S,4S)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-2-yl)ethylcarbamate (36 mg, 60%).

Workup

  1. customThe catalyst was removed through a pad of Celite
  2. concentrationThe filtrate was concentrated
  3. customChiral AD column separation (ethanol/methanol/hexane/DEA=3:2:95:0.1)

Sources & evidence

ORD record
ord-88a690ff0937423994c30b6a26f09e0b
Source dataset
uspto-grants-2011_11
Patent number
US08053603B2

Reaction notes

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