(2R,3R,7S)-7-(iodomethyl)-2,3-diphenyl-1,4-dioxaspiro[4.4]nonane → HCID 67399629, compound

HRID 70518Notes

Reaction equation

HRID 70518 reaction equation
[Na].[C:2]1([N:8]2[C:12]([SH:13])=[N:11][N:10]=[N:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH2:15][C@H:16]1[CH2:36][CH2:35][C:18]2([O:22][C@H:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C@@H:20]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:19]2)[CH2:17]1>CC(C)=O>[C:29]1([C@@H:20]2[C@@H:21]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[O:22][C:18]3([CH2:35][CH2:36][C@H:16]([CH2:15][S:13][C:12]4[N:8]([C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)[N:9]=[N:10][N:11]=4)[CH2:17]3)[O:19]2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 21051867(2R,3R,7S)-7-(iodomethyl)-2,3-diphenyl-1,4-dioxaspiro[4.4]nonaneHCID 178527989HCID 178527989, compound

Product 1

HCID 67399629HCID 67399629, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

1-Phenyl-1H-tetrazole-5-thiol sodium salt (25 g) was added to a solution of (2R,3R,7S)-7-(iodomethyl)-2,3-diphenyl-1,4-dioxaspiro[4.4]nonane (48.3 g, described in WO 2003095438) in acetone (500 mL), and the mixture was stirred at 60° C. for three hours. The solvent was evaporated from the reaction solution under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:1) to give 5-({[(2R,3R,7S)-2,3-diphenyl-1,4-dioxaspiro[4.4]non-7-yl]methyl}sulfanyl)-1-phenyl-1H-tetrazole (39.5 g) as a pale yellow oil.

Workup

  1. customThe solvent was evaporated from the reaction solution under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1→1:1)

Sources & evidence

ORD record
ord-de894345298e49c89a135827afe16ecc
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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