Ethyl Acetate → HCID 86686410, compound

HRID 632558Notes

Reaction equation

HRID 632558 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH:26]1([O:31][C:32](=[O:37])[C:33]([CH3:36])([CH3:35])[NH2:34])[CH2:30][CH2:29][CH2:28][CH2:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OCC)(=O)C>ClC(Cl)C>[CH:26]1([O:31][C:32](=[O:37])[C:33]([NH:34][CH:11]2[CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9][CH2:10]2)([CH3:35])[CH3:36])[CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 86686411HCID 86686411, compound

Product 1

HCID 86686410HCID 86686410, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of N-Boc-piperidinone (2.00 g, 10.0 mmol) in dichloroethane (25 mL) was added α,α-dimethylglycine cyclopentyl ester tosylate (3.97 g, 11.6 mmol) and sodium triacetoxyborohydride (4.248 g, 20.0 mmol). The mixture was stirred at room temperature for 22 hours then poured into ethyl acetate (300 mL). The organic layer was washed with water (3 times 100 mL), dried (MgSO4) and concentrated to yield the desired product (3.556 g, 84% yield) which was carried forward without further purification. LC/MS: m/z 355.25 [M+H]+

Workup

  1. washThe organic layer was washed with water (3 times 100 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-408d6ddca724439baed1e9817863e8fd
Source dataset
uspto-grants-2016_04
Patent number
US09321718B2

Reaction notes

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