(3AR,5R)-5-((benzyloxy)methyl)-3a,4,5,7-tetrahydro-3H-pyrano[3,4-c]isoxazole → 3,3a,4,5-tetrahydro-7H-pyrano[3,4-c]isoxazole

HRID 1427388Notes

Reaction equation

HRID 1427388 reaction equation
[CH2:1]([O:5][CH2:6][CH:7]=[N:8][OH:9])[CH2:2][CH:3]=[CH2:4].C(OC[C@@H]1OCC2=NOC[C@@H]2C1)C1C=CC=CC=1>>[N:8]1[O:9][CH2:4][CH:3]2[CH2:2][CH2:1][O:5][CH2:6][C:7]=12

Participants

3

Reactant 2

HCID 57475687(3AR,5R)-5-((benzyloxy)methyl)-3a,4,5,7-tetrahydro-3H-pyrano[3,4-c]isoxazoleHCID 722453722-(but-3-en-1-yloxy)-N-hydroxyethanimine

Product 1

HCID 574756753,3a,4,5-tetrahydro-7H-pyrano[3,4-c]isoxazoleYield 85%

Procedure

Compound C8 was prepared from 2-(but-3-en-1-yloxy)-N-hydroxyethanimine (C7) according to the general procedure for the synthesis of (3aR,5R)-5-[(benzyloxy)methyl]-3,3a,4,5-tetrahydro-7H-pyrano[3,4-c][1,2]oxazole (P1) in Preparation 1. The product was obtained as a yellow oil. Yield: 4.1 g, 32 mmol, 77%; 85% yield based on recovered starting material. 1H NMR (400 MHz, CDCl3) δ 1.73-1.84 (m, 1H), 2.13-2.20 (m, 1H), 3.34-3.45 (m, 1H), 3.50 (ddd, J=12.3, 12.1, 2.0 Hz, 1H), 3.79 (dd, J=11.6, 8.1 Hz, 1H), 4.03-4.09 (m, 1H), 4.12 (dd, J=13.5, 1.2 Hz, 1H), 4.62 (dd, J=10.2, 8.0 Hz, 1H), 4.70 (br d, J=13 Hz, 1H).

Workup

  1. customThe product was obtained as a yellow oil
  2. customon recovered

Sources & evidence

ORD record
ord-b40cf641a9f64b6198f30d1ab4c8c77e
Source dataset
uspto-grants-2015_01
Patent number
US08933221B2

Reaction notes

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