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Sodium Carbonate → Cis-8-Benzyl 3-Tert-Butyl 3,8-Diazabicyclo[4.2.0]Octane-3,8-Dicarboxylate

HRID 2175007
Notes
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Reaction equation

HRID 2175007 reaction equation
[C@H:1]12[NH:8][CH2:7][C@H:6]1[CH2:5][CH2:4][N:3]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2]2.C([O-])([O-])=O.[Na+].[Na+].[C:22](Cl)([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>C1COCC1.O>[C@H:1]12[N:8]([C:22]([O:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:23])[CH2:7][C@H:6]1[CH2:5][CH2:4][N:3]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:2]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 16099093(1S,6R)-3-Boc-3,8-diazabicyclo[4.2.0]octane

Product 1

HCID 67086554Cis-8-Benzyl 3-Tert-Butyl 3,8-Diazabicyclo[4.2.0]Octane-3,8-DicarboxylateYield 101.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×
HCID 8028TetrahydrofuranSolvent

Procedure

To (1S,6R)-tert-butyl 3,8-diazabicyclo[4.2.0]octane-3-carboxylate (1.4 g, 6.8 mmol) in THF (35 mL) and H2O (35 mL) was added Na2CO3 (1.4 g. 13.6 mmol) and CbzCl (1.1 mL, 7.5 mmol). After 18 h, the reaction mix was diluted with H2O and extracted with CH2Cl2 (2×). The combined organics were dried (Na2SO4) to give 2.4 g of the title compound as a clear oil that was used without further purification.

Workup

  1. additionthe reaction mix
  2. extractionextracted with CH2Cl2 (2×)
  3. dry with materialThe combined organics were dried (Na2SO4)

Sources & evidence

ORD record
ord-84f9e8c1a35a41ddada021d391256adb
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09062044B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes