Ethanol → HCID 69226506, compound

HRID 1510209Notes

Reaction equation

HRID 1510209 reaction equation
[CH:1]([O:14][CH2:15][CH2:16][C:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH:22]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23](O)[CH3:24].[C:26]([O:29][C:30](=[O:32])[CH3:31])(=O)[CH3:27]>N1C=CC=CC=1>[C:30]([O:29][C@@H:26]([C:24]1[CH:23]=[CH:3][CH:2]=[CH:1][CH:8]=1)[CH2:27][N:20]1[CH2:19][CH2:18][C:17]([CH2:16][CH2:15][O:14][CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:22][CH2:21]1)(=[O:32])[CH3:31]

Participants

5

Reactant 3

HCID 702EthanolHCID 7918Acetic AnhydrideHCID 67057593HCID 67057593, compound

Product 1

HCID 69226506HCID 69226506, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

With reference to FIG. 8, 4-(2-(benzhydryloxy)ethyl)-1,2,3,6-tetrahydropyridine 5 (0.5 g, 1.704 mmol), S-styrene oxide 6b (0.205 g, 1.704 mmol), ethanol (20 ml). Yield (after purification)=0.65 g. For acetylation, the mixture of regioisomers (0.5 g, 1.209 mmol), pyridine (10 ml) and acetic anhydride (0.148 ml, 1.571 mmol, 1.3 equiv). Yield (after purification)=0.2 g. 1H-NMR (CDCl3; 400 MHz): 2.03-2.07 (brs, 5H, H-3, COCH3), 2.31-2.34 (t, 2H, J=6.4 Hz, OCH2CH2), 2.59-2.74 (m, 3H, H-2, NCHHCHOAc), 2.95-2.30 (dd, 1H, J=9.2 Hz, NCHHCHOAc), 3.04 (brs, 2H, H-6), 3.51-3.54 (t, 2H, OCH2CH2), 5.33 (s, 1H, PhCH(O)Ph), 5.39 (brs, 1H, CH═C), 5.96-6.00 (dd, 1H, CHOAc), 7.21-7.37 (m, 15H, ArH). [a]25D=+21.17° (c=1.02, CHCl3).

Workup

  1. customYield
  2. custom(after purification)=0.65 g
  3. customYield
  4. custom(after purification)=0.2 g

Sources & evidence

ORD record
ord-33e897702b2c4e0d93553e68f29c77f6
Source dataset
uspto-grants-2012_07
Patent number
US08211916B2

Reaction notes

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