Boc-N-Me-Phe-OH → N-Boc-N-methyl-3-cyclohexanyl-L-alanine

HRID 2412966Notes

Reaction equation

HRID 2412966 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:20])[C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>O1CCCC1.[Rh]>[C:1]([O:5][C:6]([N:8]([CH3:20])[C@H:9]([C:17]([OH:19])=[O:18])[CH2:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 2

HCID 7010602Boc-N-Me-Phe-OHHCID 178418361HCID 178418361, compound

Product 1

HCID 66590605N-Boc-N-methyl-3-cyclohexanyl-L-alanineYield 71.4%

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.8 g of t-butoxycarbonyl-N-methylphenylalanine in 150 ml of tetrahydrofuran was hydrogenated at 60° for about four days using 60 psi hydrogen gas and 5% rhodium on carbon. The mixture was filtered and the filtrate concentrated to give the title compound (3.5 g) as a colorless oil. The oil was used without further purification. Structure assignment was supported by the nmr spectrum (loss of aromatic protons and appearance of cyclohexyl protons) and by elemental analysis.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-9cf0faee1dfe4c299a86aea6e7c35c15
Source dataset
uspto-grants-1985_01
Patent number
US04495178

Reaction notes

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