HCID 70131012, compound → HCID 70130482, compound

HRID 1936974Notes

Reaction equation

HRID 1936974 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 70131012HCID 70131012, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70130482HCID 70130482, compoundYield 82.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2S)-1-[N-((S)-1-phenylethyl)-((6S)-3-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (0.65 g) and 10% palladium on activated carbon (50% wet, 0.20 g) in ethanol (6 ml) and tetrahydrofuran (3 ml) was stirred at room temperature in the presence of hydrogen at an atmospheric pressure for 1 hour, and filtered. The filtrate was evaporated in vacuo. The residue was chromatographed (chloroform-methanol) over silica gel to afford (2S)-1-[((6S)-3-ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (430 mg). (2S)-1-[((6S)-3-Ethoxycarbonylmethoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol (190 mg) was treated with 4N hydrogen chloride in ethyl acetate to afford (2S)-1-[((6S)-3-ethoxycarbonyl-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-3-phenoxy-2-propanol hydrochloride (103 mg).

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-dd6998c84faa4c19a12b957cb54abbc4
Source dataset
uspto-grants-2002_05
Patent number
US06391915B2

Reaction notes

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