(R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoate → (R)-ethyl 5-(tert-butoxycarbonylamino)hexanoate

HRID 529549Notes

Reaction equation

HRID 529549 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:18])[CH2:10]/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:18])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 86706226(R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoateHCID 178418361HCID 178418361, compound

Product 1

HCID 86706227(R)-ethyl 5-(tert-butoxycarbonylamino)hexanoateYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of (R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoate (1.70 g, 6.61 mmol) and 5% Pd/C (350 mg) in ethanol (35 mL) was vigorously stirred under the atmosphere of hydrogen balloon for 1.5 hr. The reaction mixture was filtered and the filtrate were concentrated to give (R)-ethyl 5-(tert-butoxycarbonylamino)hexanoate (1.71 g, 6.58 mmol, 100% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 4.34 (s, 1H), 4.12 (q, J=7.1 Hz, 2H), 3.66 (s, 1H), 2.31 (td, J=7.5, 1.6 Hz, 2H), 1.75-1.57 (m, 2H), 1.51-1.38 (m, 2H), 1.44 (s, 9H), 1.25 (t, J=7.1 Hz, 3H), 1.12 (d, J=6.6 Hz, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate were concentrated

Sources & evidence

ORD record
ord-9f7832225c3a45bbb1469db306250068
Source dataset
uspto-grants-2016_05
Patent number
US09346852B2

Reaction notes

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