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Formaldehyde → tert-Butyl 5-(4-(3-((4-fluorophenyl)(methyl)amino)propyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

HRID 710346
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 710346
[C:1]([O:5][C:6](=[O:35])[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][NH:27][C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=3)=[CH:20][CH:19]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C=O.[CH3:38]CN(C(C)C)C(C)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>O.ClCCCl.CC(O)=O.C(Cl)Cl>[F:34][C:31]1[CH:32]=[CH:33][C:28]([N:27]([CH3:38])[CH2:26][CH2:25][CH2:24][C:21]2[CH:22]=[CH:23][C:18]([CH2:17][CH2:16][C:8]3([NH:7][C:6](=[O:35])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]3)=[CH:19][CH:20]=2)=[CH:29][CH:30]=1
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Komponenten

9

Edukt 4

HCID 712FormaldehydeHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 131733946tert-Butyl-5-(4-(3-(4-fluorophenylamino)propyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Produkt 1

HCID 131733947tert-Butyl 5-(4-(3-((4-fluorophenyl)(methyl)amino)propyl)phenethyl)-2,2-dimethyl-1,3-dioxan-5-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 111,2-DichloroethaneKatalysatorHCID 176Acetic AcidKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred solution of the product of Step C (0.04 g, 0.08 mmol), formaldehyde solution in H2O (0.25 ml) in 1,2-dichloroethane (5 ml) 4 drops of DIPEA was added at room temperature, followed by 5 drops of AcOH and NaBH(OAc)3 (0.04 g, 0.19 mmol). The mixture was stirred overnight at room temperature and diluted to 20 ml with CH2Cl2. The organic layer was washed with aqueous NaHCO3, H2O, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2) to give the product (0.035 g), as creamy paste. 1H-NMR (CDCl3) 1.40 (s, 3H); 1.42 (s, 3H); 1.46 (s, 9H); 1.84-1.99 (m, 4H); 2.5-2.61 (m, 4H); 2.85 (s, 3H); 3.25 (tr, 2H, J=7.41 Hz); 3.66 (d, 2H, J=11.8 Hz); 3.88 (d, 2H, J=11.7 Hz); 4.85 (s, 1H); 6.54-6.59 (m, 2H); 6.86-6.92 (m, 2H); 7.07 (s, 4H).

Aufarbeitung

  1. washThe organic layer was washed with aqueous NaHCO3, H2O
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness
  5. customthe residue was purified by FCC (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-cbbf0595e4e148e4bfd2d6a0d6f7165c
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09181182B2

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