Ethanol → HCID 69227655, compound

HRID 1510208Notes

Reaction equation

HRID 1510208 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]1[O:25][C@@H:24]1[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH2:32]([OH:34])[CH3:33].C(OC(=O)C)(=O)C>N1C=CC=CC=1>[C:32]([O:25][C@H:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:23][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:34])[CH3:33]

Participants

6

Reactant 4

HCID 702EthanolHCID 7918Acetic AnhydrideHCID 114705(+)-Styrene oxideHCID 67057593HCID 67057593, compound

Product 1

HCID 69227655HCID 69227655, 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), R-styrene oxide 6a (0.205 g, 1.704 mmol), ethanol (20 ml). Yield (after purification)=0.7 g. For acetylation, the mixture of regioisomers (0.7 g, 1.693 mmol), pyridine (10 ml) and acetic anhydride (0.208 ml, 2.2 mmol, 1.3 equiv). Yield (after purification)=0.26 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), 2.54-2.71 (m, 3H, H-2, NCHHCHOAc), 2.91-2.97 (dd, 1H, J=8.8 Hz, NCHHCHOAc), 3.04 (brs, 2H, H-6), 3.51-3.54 (t, 2H, OCH2CH2), 5.34 (s, 1H, PhCH(O)Ph), 5.39 (brs, 1H, CH═C), 5.95-5.98 (dd, 1H, CHOAc), 7.03-7.34 (m, 15H, ArH). [a]25D=−20.22° (c=1.05, CHCl3).

Workup

  1. customYield
  2. custom(after purification)=0.7 g
  3. customYield
  4. custom(after purification)=0.26 g

Sources & evidence

ORD record
ord-bbd18ef3927e4a56b63931ef02f42cb7
Source dataset
uspto-grants-2012_07
Patent number
US08211916B2

Reaction notes

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