Phosgene → 8-(Benzyloxymethyl)-1-oxa-3-azaspiro[4.5]decan-2-one

HRID 574973Notes

Reaction equation

HRID 574973 reaction equation
[NH2:1][CH2:2][C:3]1([OH:18])[CH2:8][CH2:7][CH:6]([CH2:9][O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:5][CH2:4]1.[OH-].[K+].[C:21](Cl)(Cl)=[O:22]>C1(C)C=CC=CC=1.O>[CH2:11]([O:10][CH2:9][CH:6]1[CH2:5][CH2:4][C:3]2([O:18][C:21](=[O:22])[NH:1][CH2:2]2)[CH2:8][CH2:7]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 6371PhosgeneHCID 14797Potassium HydroxideHCID 589236101-(Aminomethyl)-4-(benzyloxymethyl)cyclohexanol

Product 1

HCID 671267508-(Benzyloxymethyl)-1-oxa-3-azaspiro[4.5]decan-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of EXAMPLE 385A (475 mg) and potassium hydroxide (641 mg) in toluene (10 mL) and water (25 mL) was cooled in an ice bath and phosgene (20% in toluene, 2.178 mL) was added dropwise maintaining the temperature below 3° C. The reaction was stirred rapidly at ambient temperature for 3 hours while warming to ambient temperature. The reaction mixture was partitioned between brine (100 mL) and ethyl acetate (100 mL). The organics were dried over sodium sulfate, filtered, and concentrated to provide the title compound.

Workup

  1. temperaturemaintaining the temperature below 3° C
  2. temperaturewhile warming to ambient temperature
  3. customThe reaction mixture was partitioned between brine (100 mL) and ethyl acetate (100 mL)
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-139dd7c945204d9baf097e684fc6312b
Source dataset
uspto-grants-2015_05
Patent number
US09034875B2

Reaction notes

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