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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
ノート
印刷プレビュー

反応式

HRID 710346 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 111,2-Dichloroethane触媒HCID 176Acetic Acid触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-cbbf0595e4e148e4bfd2d6a0d6f7165c
出典データセット
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09181182B2

反応ノート

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