HCID 70130055, compound → HCID 70130581, compound

HRID 1936971Notes

Reaction equation

HRID 1936971 reaction equation
C([N:8]([CH:20]1[CH2:26][CH2:25][CH2:24][C:23]2[CH:27]=[C:28]([O:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:29]=[CH:30][C:22]=2[CH2:21]1)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH2:36]([O:35][C:33]([CH2:32][O:31][C:28]1[CH:29]=[CH:30][C:22]2[CH2:21][CH:20]([NH:8][CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:26][CH2:25][CH2:24][C:23]=2[CH:27]=1)=[O:34])[CH3:37]

Participants

5

Reactant 2

HCID 70130055HCID 70130055, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70130581HCID 70130581, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (2S)-1-[N-benzyl-(2-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (362 mg) and 10% Pd/C (50% wet, 100 mg) in ethanol (4 ml) was stirred at room temperature in the presence of hydrogen at an atmospheric pressure for 5 hours and filtered. The filtrate was evaporated in vacuo and the residue was chromatographed (dichloromethane-ethanol) over silica gel (6 g) to afford (2S)-1-[(2-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (274 mg) as a pale yellow oil. The oil (95 mg) and oxalic acid (20 mg) were dissolved in ethanol and the solution was evaporated in vacuo. The residue was powdered from ether to afford (2S)-1-[(2-ethoxycarbonylmethoxy-6,7,8, 9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol oxalate (1;1) (85 mg) as a colorless powder.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue was chromatographed (dichloromethane-ethanol) over silica gel (6 g)

Sources & evidence

ORD record
ord-c3148e2f19bb454f974eb65bfc71340a
Source dataset
uspto-grants-2002_05
Patent number
US06391915B2

Reaction notes

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