m-Chloroperbenzoic acid → tert-butyl (1S,6R)-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate

HRID 1670626Notes

Reaction equation

HRID 1670626 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH:23]=[CH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>ClCCl>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH2:21][C@@H:22]2[C@@H:23]([O:6]2)[CH2:24]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 13094787tert-Butyl 3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 55273474tert-butyl (1S,6R)-7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylateYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Add a solution of m-chloroperoxybenzoic acid (0.77 mol, 133.1 g) in dichloromethane (200 mL) drop wise to a solution of 3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.64 mol, 117.8 g) in dichloromethane (1 L) at 0° C. Upon complete addition, warm the reaction mixture to room temperature and stir for 16 h. Dilute the reaction mixture with dichloromethane and wash with 4 N sodium hydroxide solution, water, and brine. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate to obtain the title compound (112 g, 87%) as a light yellow oil. 1H NMR (400 MHz, CDCl3) δ 1.44 (s, 9H), 1.87-1.93 (m s, 1H), 2.04 (br s, 1H), 3.11 (br s, 1H), 3.20 (br s, 1H), 3.28 (s, 1H), 3.44 (br s, 1H), 3.68 (br s 1H). 3.81-3.92 (m, 1H). ES-MS m/z 204 [M+H]+.

Workup

  1. additionUpon complete addition
  2. washwash with 4 N sodium hydroxide solution, water, and brine
  3. dry with materialDry the organic layer over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-8c4a0c7b8b684982a1458a11ffb366f5
Source dataset
uspto-grants-2011_08
Patent number
US07994164B2

Reaction notes

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