(2S)-1-[N-benzyl-(1-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol → (2S)-1-[(1-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol

HRID 1936970Notes

Reaction equation

HRID 1936970 reaction equation
C([N:8]([CH:20]1[CH2:26][CH2:25][CH2:24][C:23]2[C:27]([O:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:28][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]>CO.[Pd]>[CH2:36]([O:35][C:33]([CH2:32][O:31][C:27]1[C:23]2[CH2:24][CH2:25][CH2:26][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)[CH2:21][C:22]=2[CH:30]=[CH:29][CH:28]=1)=[O:34])[CH3:37]

Participants

5

Reactant 2

HCID 9892318(2S)-1-[N-benzyl-(1-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanolHCID 178418361HCID 178418361, compound

Product 1

HCID 70131462(2S)-1-[(1-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanolYield 80.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2S)-1-[N-benzyl-(1-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (0.55 g) and 10% Pd/C (50% wet, 150 mg) in methanol (6 ml) was stirred at room temperature in the presence of hydrogen at an atmospheric pressure for 4 hours and filtered. The filtrate was evaporated in vacuo and the residue was chromatographed (chloroform-ethanol) over silica gel (8 g) to afford (2S)-1-[(1-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (365 mg) as a pale yellow solid. The solid (109 mg) was treated with 4N hydrogen chloride in ethyl acetate and powdered from ether to afford (2S)-1-[(1-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol hydrochloride (96 mg) as a colorless amorphous powder.

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated in vacuo
  3. customthe residue was chromatographed (chloroform-ethanol) over silica gel (8 g)

Sources & evidence

ORD record
ord-9fc2abab064e463a990010ca733cc5bd
Source dataset
uspto-grants-2002_05
Patent number
US06391915B2

Reaction notes

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