HCID 70132424, compound → HCID 70130671, compound

HRID 1936973Notes

Reaction equation

HRID 1936973 reaction equation
C1([C@H]([N:9]([C@@H:21]2[CH2:27][CH2:26][CH2:25][C:24]3[CH:28]=[CH:29][C:30]([O:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])=[CH:31][C:23]=3[CH2:22]2)[CH2:10][C@@H:11]([OH:20])[CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)C)C=CC=CC=1.[H][H]>[Pd].C(O)C.O1CCCC1>[CH2:37]([O:36][C:34]([CH2:33][O:32][C:30]1[CH:29]=[CH:28][C:24]2[CH2:25][CH2:26][CH2:27][C@@H:21]([NH:9][CH2:10][C@@H:11]([OH:20])[CH2:12][O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:22][C:23]=2[CH:31]=1)=[O:35])[CH3:38]

Participants

6

Reactant 2

HCID 70132424HCID 70132424, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70130671HCID 70130671, compoundYield 85.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2R)-1-[N-((R)-1-phenylethyl)-((6R)-3-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (2.0 g) and 10% palladium on activated carbon (50% wet, 0.70 g) in ethanol (24 ml) and tetrahydrofuran (12 ml) was stirred at room temperature in the presence of hydrogen at an atmospheric pressure for 3.5 hours, and filtered. The filtrate was evaporated in vacuo. The residue was chromatographed (chloroform-methanol) over silica gel to afford (2R)-1-[((6R)-3-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (1.37 g).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated in vacuo
  3. customThe residue was chromatographed (chloroform-methanol) over silica gel

Sources & evidence

ORD record
ord-4d56b24bee86493c8b5f4576c0d92cdb
Source dataset
uspto-grants-2002_05
Patent number
US06391915B2

Reaction notes

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