Sodium Hydroxide → HCID 86584011, compound

HRID 2303392Notes

Reaction equation

HRID 2303392 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH:15]=[C:14]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C(Cl)C=C(C(OO)=[O:32])C=1.[OH-].[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][C@:14]2([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C@@H:15]([O:32]2)[CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 22959133HCID 22959133, compound

Product 1

HCID 86584011HCID 86584011, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 36.0 g (117 mmol) of 4-benzyl-3,6-dihydro-2H-pyridine-1-carboxylic acid benzyl ester in 250 ml CH2Cl2 were added 40.9 g (166 mmol, ˜70%) MCPBA. The reaction mixture was stirred for 2 hours and a 1N NaOH-solution was added. The aqueous phase was extracted twice with CH2Cl2 and the combined organic layers were washed with 1 N NaOH, dried over MgSO4 and the solvent was removed under reduced pressure to give 37.6 g (116 mmol, 99%) of (1R,6S) and (1S,6R)-6-benzyl-7-oxa-3-aza-bicyclo[4.1.0]heptane-3-carboxylic acid benzyl ester as an oil.

Workup

  1. extractionThe aqueous phase was extracted twice with CH2Cl2
  2. washthe combined organic layers were washed with 1 N NaOH
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-385e80ce2e014e648e6a052ccadc8467
Source dataset
uspto-grants-2002_08
Patent number
US06432985B1

Reaction notes

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