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Bromochloromethane → (4S)-N-tert-butoxycarbonyl-5-chloromethyl-5-hydroxy-4-phenylmethyloxazolidine

HRID 1071876
Notes
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Reaction equation

HRID 1071876 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11](=[O:20])[O:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][Cl:23].C([Li])CCC.S([O-])(O)(=O)=O.[K+]>CCCCCC.O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:11]([CH2:22][Cl:23])([OH:20])[O:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6333BromochloromethaneHCID 516920Potassium bisulfateHCID 11482799(4S)-N-Boc-4-phenylmethyloxazolidin-5-oneHCID 178418339Butyllithium

Product 1

HCID 15549468(4S)-N-tert-butoxycarbonyl-5-chloromethyl-5-hydroxy-4-phenylmethyloxazolidineYield 100%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

(4S)-N-tert-butoxycarbonyl-4-phenylmethyloxazolidin-5-one (0.34 g) and bromochloromethane (0.10 ml) were added to dehydrated tetrahydrofuran (12 ml). After cooling to −78° C., 1.53 M solution (1.03 ml) of n-butyllithium in hexane was added to the obtained mixture, and they were stirred for 1 hour. 10% aqueous potassium hydrogensulfate solution was added to the reaction mixture to terminate the reaction. The temperature of the reaction mixture was elevated to room temperature. After the extraction with ethyl acetate twice, the obtained ethyl acetate layer was dried over anhydrous magnesium sulfate and then magnesium sulfate was removed. The solvent was evaporated under reduced pressure to obtain intended (4S)-N-tert-butoxycarbonyl-5-chloromethyl-5-hydroxy-4-phenylmethyloxazolidine (0.40 g) in a yield of 100%.

Workup

  1. customto terminate
  2. customthe reaction
  3. customwas elevated to room temperature
  4. extractionAfter the extraction with ethyl acetate twice
  5. dry with materialthe obtained ethyl acetate layer was dried over anhydrous magnesium sulfate
  6. custommagnesium sulfate was removed
  7. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-fbc5a02748ea459bb83d9b5a0ccceac1
Source dataset
uspto-grants-2005_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06906224B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes