Dichloromethane → 3-Phenyl-8-carbobenzyloxy-1-oxa-3,8-diazaspiro[4.5]decan-2-one

HRID 127262Notes

Reaction equation

HRID 127262 reaction equation
[C:1]([N:11]1[CH2:16][CH2:15][C:14]([OH:25])([CH2:17][NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:13][CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C.ClCCl.[C:36](Cl)(Cl)=[O:37]>C1(C)C=CC=CC=1>[C:19]1([N:18]2[CH2:17][C:14]3([CH2:13][CH2:12][N:11]([C:1]([O:3][CH2:4][C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=4)=[O:2])[CH2:16][CH2:15]3)[O:25][C:36]2=[O:37])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6371PhosgeneHCID 8471TriethylamineHCID 20286530Benzyl 4-hydroxy-4-[(phenylamino)methyl]piperidine-1-carboxylate

Product 1

HCID 130165993-Phenyl-8-carbobenzyloxy-1-oxa-3,8-diazaspiro[4.5]decan-2-oneYield 50.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2.2 g 1-carbobenzyloxy-4-hydroxy-4-anilinomethylpiperidine, 3 ml triethylamine and 20 ml dichloromethane is added a solution of 3 g phosgene in 25 ml toluene. After 30 minutes the mixture is washed with 100 ml, 1 N hydrochloric acid. Removal of solvent by evaporation followed by recrystallization from diethyl ether-hexane affords 1.2 g of 3-phenyl-8-carbobenzyloxy-1-oxa-3,8-diazaspiro[4.5]decan-2-one, mp 100°-102°.

Workup

  1. washAfter 30 minutes the mixture is washed with 100 ml, 1 N hydrochloric acid
  2. customRemoval of solvent
  3. customby evaporation
  4. customfollowed by recrystallization from diethyl ether-hexane

Sources & evidence

ORD record
ord-a2446ea98dcb4f4fa5ebe75ee8f81ed0
Source dataset
uspto-grants-1981_03
Patent number
US04255432

Reaction notes

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