Hydrochloric Acid → 8-Carbobenzyloxy-1-oxa-3,8-diazaspiro[4.5]decan-2-one

HRID 127264

Reaction equation

HRID 127264 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][NH:3][C:2]1=[O:11].C(=O)(O)[O-].[Na+].Cl[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].Cl>O>[C:18]([N:8]1[CH2:7][CH2:6][C:5]2([O:1][C:2](=[O:11])[NH:3][CH2:4]2)[CH2:10][CH2:9]1)([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 129541141-Oxa-3,8-diazaspiro(4.5)decan 2-one

Product 1

HCID 130165958-Carbobenzyloxy-1-oxa-3,8-diazaspiro[4.5]decan-2-oneYield 81.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 9.5 g 1-oxa-3,8-diazaspiro[4.5]decan-2-one and 75 ml water, at 0°, is added 6.3 g sodium bicarbonate and 10.9 g benzyl chloroformate. The mixture is stirred 18 hours at 0°, acidified with 10 N hydrochloric acid and stirred four hours at room temperature. The mixture is extracted with three 50 ml portions of dichloromethane. Removal of solvent affords 14.4 g 8-carbobenzyloxy-1-oxa-3,8-diazaspiro[4.5]decan-2-one, mp 126°-128°.

Workup

  1. stirringstirred four hours at room temperature
  2. extractionThe mixture is extracted with three 50 ml portions of dichloromethane
  3. customRemoval of solvent

Sources & evidence

ORD record
ord-33202028d3524476be3805df397f91a2
Source dataset
uspto-grants-1981_03
Patent number
US04255432

Linked notes

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