1-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one → 1-Ethyl-2-(4-benzyloxyphenyl)-8-hydroxymethylindolizine

HRID 1422109Notes

Reaction equation

HRID 1422109 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([CH2:9][CH2:10][CH3:11])=[N:5][CH:6]=[CH:7][CH:8]=1.[CH2:12]([O:19][C:20]1[CH:29]=[CH:28][C:23]([C:24](=O)[CH2:25]Br)=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[CH2:10]([C:9]1[C:24]([C:23]2[CH:28]=[CH:29][C:20]([O:19][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:21][CH:22]=2)=[CH:25][N:5]2[C:4]=1[C:3]([CH2:2][OH:1])=[CH:8][CH:7]=[CH:6]2)[CH3:11]

Participants

3

Reactant 2

HCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-oneHCID 18707030Hydroxymethyl-2-n-propylpyridin

Product 1

HCID 187069521-Ethyl-2-(4-benzyloxyphenyl)-8-hydroxymethylindolizineYield 83%

Procedure

3-Hydroxymethyl-2-n-propylpyridin was reacted with 4-benzyloxyphenacylbromide by the general synthetic principles outlined in example 1, step 2, to afford 1-ethyl-2-(4-benzyloxyphenyl)-8-hydroxymethylindolizine as yellow crystals in 83% yield. M.p. 144-145° C. MS(SP): m/z 357 (M+). 1H--NMR (DMSO-d6, 200 MHz) δ: 1.08 (t, 3 H); 2.83 (q, 2 H); 4.73 (d, 2 H); 5.12 (s, 2 H); 5.22 (t, 1 H); 6.43 (dd, 1 H); 6.66 (d, 1 H); 7.07 (d, 2 H); 7.28-7.53 (m, 8 H); 8.04 (d, 1 H).

Sources & evidence

ORD record
ord-380aba6e240640b684aa46cd0dcd0499
Source dataset
uspto-grants-2000_06
Patent number
US06080754

Reaction notes

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