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Water → tert-butyl (3RS,4SR)-4-(3,4-dichlorophenyl)-1,5-dioxa-8-azaspiro[2.6]nonane-8-carboxylate

HRID 1022677
Notes
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Reaction equation

HRID 1022677 reaction equation
C[Li].[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][C:12]2=[O:25])[CH:7]=[CH:8][C:9]=1[Cl:10].I[CH2:27]I.O>C(OCC)C.C1COCC1>[Cl:3][C:4]1[CH:5]=[C:6]([CH:11]2[O:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:13][C:12]32[O:25][CH2:27]3)[CH:7]=[CH:8][C:9]=1[Cl:10]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 6346DiiodomethaneHCID 66976649HCID 66976649, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 86663865tert-butyl (3RS,4SR)-4-(3,4-dichlorophenyl)-1,5-dioxa-8-azaspiro[2.6]nonane-8-carboxylateYield 18.9%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution (3 M, 0.56 mL) of methyllithium in diethyl ether was added to a solution of tert-butyl (7RS)-7-(3,4-dichlorophenyl)-6-oxo-1,4-oxazepane-4-carboxylate (300 mg) and diiodomethane (335 mg) in THF (3 mL), and the mixture was stirred at 0° C. for 30 min, and at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography and HPLC to give the title compound (59 mg).

Workup

  1. waitat room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography and HPLC

Sources & evidence

ORD record
ord-ee75f13362074becadb02eff9adece36
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722662B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes