HCID 131723377, compound → HCID 131723376, compound

HRID 2228381Notes

Reaction equation

HRID 2228381 reaction equation
[CH3:1][O:2][C:3](=[O:22])/[C:4](/[NH:18][C:19](=[O:21])[CH3:20])=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]=[CH2:14])=[CH:8][C:7]=1[SiH:15]([CH3:17])[CH3:16]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:22])[C@@H:4]([NH:18][C:19](=[O:21])[CH3:20])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]=[CH2:14])=[CH:8][C:7]=1[SiH:15]([CH3:16])[CH3:17]

Participants

3

Reactant 1

HCID 131723377HCID 131723377, compound

Product 1

HCID 131723376HCID 131723376, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottomed flask containing (2Z)-methyl-2-acetamido-3-(4-allyldimethylsilylphenyl)prop-2-enoate (1 Scheme 5, 3.2 g, 10 mmol) in deoxygenated CH2Cl2 (40 mL) was added [(COD)Rh(S,S)-Et-DuPHOS]OTf(7 mg). After eight vacuum/H2 cycles, the reaction was stirred for 23 h at room temperature under H2 (1 atm). Once the reaction was finished, the solution was passed through a short plug of silica to remove the catalyst to afford a colorless oil (3.2 g. 100%); 1H NMR (300 MHz, CDCl3) δ 0.25 (s, 6 H), 1.72 (dd, J=8.10 Hz, 2 H), 1.98 (s, 3 H), 3.10 (m, 2 H), 3.72 (s, 3 H), 4.81 (d, J=1.2 Hz, 1 H), 4.83-4.92 (2 H), 5.76 (m, 1 H), 5.94 (bd, J=7.80 Hz, NH, 1 H), 7.06 (d, J=7.20 Hz, 2 H), 7.42 (d, J=7.20 Hz, 2 H); 13C NMR (75 MHz, CDCl3) −3.2, 23.3, 23.9, 37.9, 52.6, 53.3, 113.7, 128.9, 134.1, 134.8, 136.9, 137.5, 170.1, 172.5; HRMS (EI) calcd for C17H25NO3Si 319.1600, found 319.1602.

Workup

  1. customto remove the catalyst
  2. customto afford a colorless oil (3.2 g. 100%)

Sources & evidence

ORD record
ord-6f1645cb20394dde804273b6bda0d4ab
Source dataset
uspto-grants-2002_07
Patent number
US06416861B1

Reaction notes

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