Diisopropylethylamine → HCID 70067440, compound

HRID 1953908Notes

Reaction equation

HRID 1953908 reaction equation
[CH:1]1([N:7]([CH3:16])[C@@H:8]([CH2:12][CH:13]([CH3:15])[CH3:14])[C:9]([OH:11])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:17](N(C(C)C)CC)(C)C.Br[CH:27]1[CH2:32][CH2:31][CH2:30][CH:29]=[CH:28]1>C1COCC1>[CH2:17]([O:10][C:9](=[O:11])[C@@H:8]([N:7]([C:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1)[CH3:16])[CH2:12][CH:13]([CH3:14])[CH3:15])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1370573-BromocyclohexeneHCID 11401906HCID 11401906, compound

Product 1

HCID 70067440HCID 70067440, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The Preparation (S)-2-(Cyclohexyl-methyl-amino)-4-methyl-pentanoic Acid (IId) ##STR31## Step i: N-Me-O-Benzyl-L-Leucine (3.6 g, 15.3 mmol) was dissolved in THF (77 mL) and treated with diisopropylethylamine (21 mL, 122 mmol) and 3-bromo-cyclohexene (3.5 mL, 30.6 mmol). The reaction was heated to 50° C. for 2 days. The reaction was filtered, and the solution was concentrated. The residue was chromatographed on silica gel eluting with 8% ethyl acetate/hexanes to give 2.75 g (57%) of (S)-2-(cyclohexenyl-methyl-amino)-4-methyl-pentanoic acid benzyl ester.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe solution was concentrated
  3. customThe residue was chromatographed on silica gel eluting with 8% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-29203e3772b94e6c9e1466b28ca47951
Source dataset
uspto-grants-2000_09
Patent number
US06117841

Reaction notes

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