Dichloromethane → HCID 178524483, compound

HRID 1639963Notes

Reaction equation

HRID 1639963 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-b005b1bf05584ffa81c3803c7b9b6b2c
Source dataset
uspto-grants-2012_02
Patent number
US08110581B2

Reaction notes

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