Acetic Acid → HCID 11951207, compound

HRID 507857Notes

Reaction equation

HRID 507857 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([N:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1)[CH2:10]2)=[O:5])[CH3:2].[CH2:21]([NH:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:22].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl>[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([N:14]1[CH2:19][CH2:18][CH:17]([N:23]([CH2:21][CH3:22])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:16][CH2:15]1)[CH2:10]2)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7670N-EthylanilineHCID 5049666Sodium triacetoxyborohydrideHCID 59434285HCID 59434285, compound

Product 1

HCID 11951207HCID 11951207, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

3-(4-Oxo-piperidin-1-yl)-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid ethyl ester 2 (200.000 mg; 0.713 mmol; 1.000 eq.) was dissolved in DCE (4 mL) and treated with TEA (87.821 uL; 63.758 mg; 0.631 mmol; 1.000 eq.) and ethylaniline (91.79 mg; 0.856 mmol; 1.200 eq.), followed by NaBH(OAc)3 (453.569 mg; 2.140 mmol; 3.000 eq.) and AcOH (40.870 uL; 42.873 mg; 0.713 mmol; 1.000 eq.). The reaction was allowed to stir at room temperature for 48 hr and was quenched with MeOH (3 mL). The quenched mixture was allowed to stir at room temperature for 2 hrs, and the resulting suspension was filtered through a syringe filter. A 1 mL aliquot of the filtrate was purified by LC/MS (1 mL injection, 10-99 CH3CN gradient with 0.03% TFA, 15 minute run) to provide a pure sample of the desired product. LC/MS M/Z 372.2, retention time=1.82 minutes, 10-99% CH3CN/H2O gradient with 0.05% TFA.

Workup

  1. customwas quenched with MeOH (3 mL)
  2. stirringto stir at room temperature for 2 hrs
  3. filtrationthe resulting suspension was filtered through a syringe
  4. filtrationfilter
  5. customA 1 mL aliquot of the filtrate was purified by LC/MS (1 mL injection, 10-99 CH3CN gradient with 0.03% TFA, 15 minute run)

Sources & evidence

ORD record
ord-56890da9cf1b44b3b145faf5e7a1ff5c
Source dataset
uspto-grants-2010_08
Patent number
US07786308B2

Reaction notes

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