Sodium Hydroxide → 4-Cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one

HRID 1525853Notes

Reaction equation

HRID 1525853 reaction equation
Cl.[CH:2]1([N:5]2[CH2:10][C:9]3([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[O:8][CH2:7][C:6]2=[O:16])[CH2:4][CH2:3]1.[OH-].[Na+]>ClCCl.O>[CH:2]1([N:5]2[CH2:10][C:9]3([CH2:11][CH2:12][NH:13][CH2:14][CH2:15]3)[O:8][CH2:7][C:6]2=[O:16])[CH2:4][CH2:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69083351HCID 69083351, compound

Product 1

HCID 667837534-Cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-oneYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 4-cyclopropyl-1-oxa-4,9-diazaspiro[5.5]undecan-3-one hydrochloride (8.11 mmol) in dichloromethane (10 mL) was treated with 1N aq NaOH (10.00 mmol). The biphasic mixture was stirred for 1 hour, at which point the cloudy organic layer had turned clear. The contents of the flask were further diluted with water (50 mL) and dichloromethane (50 mL) and the layers were separated. The aqueous layer was extracted with dichloromethane. The organic layers were combined, dried over sodium sulfate, filtered and concentrated in vacuo to afford the title compound as a yellow oil (80%). MS(ES)+ m/e 211.2 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with dichloromethane
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17f6540727ff438496b2f0e83f98c8a1
Source dataset
uspto-grants-2015_07
Patent number
US09084794B2

Reaction notes

Loading…