Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine → HCID 131726063, compound

HRID 722395Notes

Reaction equation

HRID 722395 reaction equation
[CH2:1]([O:3][C:4](=[O:23])/[CH:5]=[CH:6]/[C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:8]=1)[CH3:2].CO[CH2:26][N:27]([CH2:35][Si](C)(C)C)[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>ClCCl.FC(F)(F)C(O)=O>[C:19]([O:18][C:16]([N:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([C@H:6]2[C@H:5]([C:4]([O:3][CH2:1][CH3:2])=[O:23])[CH2:35][N:27]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:26]2)=[CH:8]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine2×HCID 21884270HCID 21884270, compound

Product 1

HCID 131726063HCID 131726063, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalyst2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of trans-tert-butyl 3-(3-ethoxy-3-oxoprop-1-enyl)-1H-indole-1-carboxylate (2.70 g, 8.57 mmol) and N-(methoxymethyl)(phenyl)-N-((trimethylsilyl)methyl)methanamine (2.21 mL) in dichloromethane (11 mL) was added 4 drops of trifluoroacetic acid and the mixture was stirred at 40° C. for 1 hr. Then another 0.15 mL of N-(methoxymethyl)(phenyl)-N-((trimethylsilyl)methyl)methanamine and 2 drop of trifluoroacetic acid were added and the mixture was stirred at 40° C. for another 2 hr. After cooling down to room temperature, the mixture was concentrated under vacuum to give the title compound as a pale yellow sticky oil (quantitative yield). 1H NMR (400 MHz, CDCl3) δ 1.21 (3H, t, J=7.2 Hz), 1.65 (9H, s), 2.86 (2H, q, J=8 Hz), 3.03 (1H, t, J=8 Hz), 3.11 (1H, t, J=8 Hz), 3.19 (1H, q, J=8 Hz), 3.70 (2H, dd, J=16 28 Hz), 3.91 (1H, q, J=8 Hz), 4.13 (2H, q, J=8 Hz), 7.20–7.38 (7H, m), 7.45 (1H, s), 7.74 (1H, d, J=8 Hz), 8.10 (1H, brd s). HPLC purity (retention time): 100% (1.84 min, method C). MS: 449.38 (M+Na+).

Workup

  1. stirringthe mixture was stirred at 40° C. for another 2 hr
  2. temperatureAfter cooling down to room temperature
  3. concentrationthe mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-0d4789251e0e44579a7cd7ff072fb872
Source dataset
uspto-grants-2006_11
Patent number
US07138423B2

Reaction notes

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