Acetic Acid → HCID 66953653, compound

HRID 1511793Notes

Reaction equation

HRID 1511793 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=O)[CH2:10][CH:9]1[CH2:14][O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH:29][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:10][C@H:9]1[CH2:14][O:15][C:16](=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 66734029HCID 66734029, compound

Product 1

HCID 66953653HCID 66953653, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-(2,2-dimethyl-propionyloxymethyl)-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (prepared according to WO2007017828, 8.0 g, 26.7 mmol) and benzylamine (2.9 mL, 1 eq) in DCE (100 mL) were added NaBH(OAc)3 (7.9 g, 1.4 eq) and AcOH (1.53 mL, 1 eq) and the resulting solution was stirred at rt for 1 h. The mixture was quenched by adding NH4OH and the aq. layer was extracted with EA. The combined org. layers were washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by CC (DCM/MeOH/NH4OH 1000:25:2) to afford the title intermediate as a yellow oil (10.2 g, 98%).

Workup

  1. customThe mixture was quenched
  2. additionby adding NH4OH
  3. extractionthe aq. layer was extracted with EA
  4. washlayers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by CC (DCM/MeOH/NH4OH 1000:25:2)

Sources & evidence

ORD record
ord-814703dee34846f190e9c9badb58e75e
Source dataset
uspto-grants-2012_07
Patent number
US08217029B2

Reaction notes

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