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Nitrogen → (8-(4-Chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methyl dimethylcarbamate

HRID 15746
Notes
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Reaction equation

HRID 15746 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:20]([CH2:21][CH3:22])[CH2:19][C:14]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:13][CH:12]2[CH2:23][OH:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.N#N.[CH3:34][N:35]([CH3:39])[C:36](Cl)=[O:37]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:34][N:35]([CH3:39])[C:36](=[O:37])[O:24][CH2:23][CH:12]1[N:11]([S:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH:20]([CH2:21][CH3:22])[CH2:19][C:14]2([O:18][CH2:17][CH2:16][O:15]2)[CH2:13]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 947NitrogenHCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 59342380(8-(4-Chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methanol

Product 1

HCID 59342408(8-(4-Chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methyl dimethylcarbamateYield 136.6%

Reagents, catalysts & solvents

2
HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(8-(4-Chlorophenylsulfonyl)-9-ethyl-1,4-dioxa-8-azaspiro[4.5]decan-7-yl)methanol (111; 1.19 g, 3.18 mmol) and triethylamine (2.21 ml, 15.9 mmol) were added to CH2Cl2 (15 mL) in a flame-dried flask and placed tinder N2. DMAP (77.8 mg, 0.637 mmol) was added and the mixture stirred for 5 minutes. Dimethylcarbamoyl chloride (0.88 mL, 1.54 mmol) was added dropwise and the reaction stirred for 18 hours. The reaction mixture was concentrated under reduced pressure, and equal portions of EtOAc and water were added. The aqueous layer was extracted with several more portions of EtOAc. The combined organic layers were washed with a dilute NaOH solution, 10% citric acid, brine, dried over Na2SO4 and concentrated to yield 940 mg of 112 as a yellow oil. The material was purified by column chromatography using EtOAc/hexanes gradients to yield 836 mg (59%) of a mixture of cis/trans isomers.

Workup

  1. stirringthe reaction stirred for 18 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure, and equal portions of EtOAc and water
  3. additionwere added
  4. extractionThe aqueous layer was extracted with several more portions of EtOAc
  5. washThe combined organic layers were washed with a dilute NaOH solution, 10% citric acid, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-2d6a559f17e04d37922fd5bb09eb2b92
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07732609B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes