Sodium Acetate → tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylate

HRID 260132Notes

Reaction equation

HRID 260132 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[CH3:12][C:13]([O-])=[O:14].[Na+].[C:17]([O:21][C:22](NN1CCC(CCO)CC1)=[O:23])([CH3:20])([CH3:19])[CH3:18]>C(Cl)Cl.CCOCC>[C:17]([O:21][C:22]([N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][CH:13]=[O:14])[CH2:8][CH2:7]1)=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 22402467HCID 22402467, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 10353694tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of CH2Cl2 (200 mL) was treated with pyridiniumchlorochromate (PCC) (6.7 g, 0.031 mol) for five minutes. Solid NaOAc (2.55 g, 0.031 mol) and 4Å molecular sieves were added, followed by a solution of 4-1 (4.75 g, 0.02 mol) in CH2Cl2 (50 mL). The reaction was stirred for 3 h, diluted with 400 mL of Et2O, and filtered through a pad of silica gel. The silica gel was washed with 1 L of Et2O and 0.5 L of 1:1 Et2O/CHCl3. The organic solutions were combined, concentrated to give a greenish oil which was filtered through another pad of silica gel, eluting with 1.2 L of Et2O. The filtrate was concentrated to give 4-2 as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 9.77 (s, 1H), 4.08 (bd, 2H), 2.7 (bt, 2H), 2.37 (dd, 2H), 2.03 (m, 1H), 1.7 (bd, 2H), 1.42 (s, 9H), 1.2 (m, 2H). ##STR32## Methyl 2-(S)-benzyloxycarbonylamino-3-aminopropionate hydrochloride (5-2)

Workup

  1. filtrationfiltered through a pad of silica gel
  2. washThe silica gel was washed with 1 L of Et2O and 0.5 L of 1:1 Et2O/CHCl3
  3. concentrationconcentrated
  4. customto give a greenish oil which
  5. filtrationwas filtered through another pad of silica gel
  6. washeluting with 1.2 L of Et2O
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-55c33e94bc5d4df0a4f7dab102a15ec4
Source dataset
uspto-grants-1996_06
Patent number
US05525617

Reaction notes

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