Dichloromethane → HCID 178524483, compound

HRID 1044346Notes

Reaction equation

HRID 1044346 reaction equation
Cl.[OH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]2[CH2:13][CH2:12][C:11]3([CH2:18][CH2:17][CH2:16][NH:15][CH2:14]3)[C:10]2=[O:19])[CH2:5][CH2:4]1.Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)=[O:22].C(N(CC)C(C)C)(C)C.C(Cl)Cl>>[OH:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([N:9]2[CH2:13][CH2:12][C:11]3([CH2:18][CH2:17][CH2:16][N:15]([C:21]([O:23][C:24]4[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=4)=[O:22])[CH2:14]3)[C:10]2=[O:19])[CH2:5][CH2:4]1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 821294-Nitrophenyl chloroformateHCID 178479652HCID 178479652, compound

Product 1

HCID 178524483HCID 178524483, compoundYield 28.7%

Procedure

A mixture of 2-(trans-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one hydrochloride (0.30 g, 0.0010 mol), p-nitrophenyl chloroformate (0.25 g, 0.0012 mol), and N,N-diisopropylethylamine (540 μL, 0.0031 mol) in methylene chloride (4 mL, 0.06 mol) was stirred at rt for 16 h. The crude reaction mixture was purified by flash column chromatography to afford 120 mg of the desired product.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-79f6f714f3d6489a976172a6f82f6706
Source dataset
uspto-grants-2013_10
Patent number
US08563570B2

Reaction notes

Loading…