Benzyl 4-oxopiperidine-1-carboxylate → HCID 86686412, compound

HRID 632559Notes

Reaction equation

HRID 632559 reaction equation
[C:1]([N:11]1[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.[C:19]([O:23][C:24](=[O:28])[C@H:25]([CH3:27])[NH2:26])([CH3:22])([CH3:21])[CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:19]([O:23][C:24](=[O:28])[C@@H:25]([NH:26][CH:14]1[CH2:15][CH2:16][N:11]([C:1]([O:3][CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:2])[CH2:12][CH2:13]1)[CH3:27])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 11275390tert-Butyl alaninate hydrochloride

Product 1

HCID 86686412HCID 86686412, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of N-Cbz-4-piperidinone (3.497 g, 15.0 mmol) in dichloroethane (100 mL) was added L-alanine tert-butyl ester hydrochloride (2.731 g, 15.03 mmol) and sodium triacetoxyborohydride (6.47 g, 30.5 mmol). The mixture was stirred for 20 hours at room temperature, then quenched by the addition of saturated ammonium chloride (100 mL). The mixture was poured into ethyl acetate (500 mL), washed with water (2 times 100 mL), dried (MgSO4) and concentrated to yield the desired product (5.30 g, 97% yield). LC/MS: m/z 325.25 [M+H]+

Workup

  1. customquenched by the addition of saturated ammonium chloride (100 mL)
  2. additionThe mixture was poured into ethyl acetate (500 mL)
  3. washwashed with water (2 times 100 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-38ae7e601b8e48c7a7adddb1370eddf7
Source dataset
uspto-grants-2016_04
Patent number
US09321718B2

Reaction notes

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