(3AR,5R)-5-((benzyloxy)methyl)-3a,4,5,7-tetrahydro-3H-pyrano[3,4-c]isoxazole → HCID 131736522, compound

HRID 1478729Notes

Reaction equation

HRID 1478729 reaction equation
[CH:1]1([CH:4]([O:12][CH2:13][CH:14](OCC)OCC)[CH2:5]/[CH:6]=[CH:7]/[C:8]([O:10][CH3:11])=[O:9])[CH2:3][CH2:2]1.C(OC[C@H](OCC=[N:37][OH:38])CC=C)C1C=CC=CC=1.C(OC(OCC)CO[C@H](CC=C)COCC1C=CC=CC=1)C.C(OC[C@@H]1OCC2=NOC[C@@H]2C1)C1C=CC=CC=1>>[CH:1]1([CH:4]([O:12][CH2:13][CH:14]=[N:37][OH:38])[CH2:5]/[CH:6]=[CH:7]/[C:8]([O:10][CH3:11])=[O:9])[CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 57475687(3AR,5R)-5-((benzyloxy)methyl)-3a,4,5,7-tetrahydro-3H-pyrano[3,4-c]isoxazoleHCID 59281174[(R)-2-(2,2-diethoxyethoxy)-4-pentenyloxymethyl]benzeneHCID 86640913((R)-1-benzyloxymethyl-3-butenyloxy)acetaldehyde oximeHCID 90253559methyl (2E)-5-cyclopropyl-5-(2,2-diethoxyethoxyl)pent-2-enoate

Product 1

HCID 131736522HCID 131736522, compound

Procedure

Methyl (2E)-5-cyclopropyl-5-(2,2-diethoxyethoxyl)pent-2-enoate (C34) was converted to the product using the method described for synthesis of 2-{[(2R)-1-(benzyloxy)pent-4-en-2-yl]oxy}-N-hydroxyethanimine (C3) in the section “Alternate conversion of C2 to C4.” The product was obtained as an oil: 1H NMR analysis indicated a roughly 1:1 mixture of geometric isomers around the oxime. Yield: 3.50 g, 15.4 mmol, 73%. 1H NMR (400 MHz, CDCl3) δ 7.73 and 7.47 (2 br s, total 1H), [7.49 (dd, J=5.8, 5.6 Hz) and 6.90 (dd, J=3.7, 3.6 Hz), total 1H], 6.99-7.09 (m, 1H), 5.87-5.93 (m, 1H), [4.54 (dd, half of ABX pattern, J=16.1, 3.6 Hz), 4.37 (dd, half of ABX pattern, J=16.0, 3.7 Hz), 4.28 (dd, half of ABX pattern, J=12.8, 5.5 Hz) and 4.14 (dd, half of ABX pattern, J=12.7, 5.8 Hz), total 2H], 3.74 and 3.74 (2 s, total 3H), 2.71-2.81 (m, 1H), 2.51-2.57 (m, 2H), 0.80-0.90 (m, 1H), 0.63-0.72 (m, 1H), 0.48-0.57 (m, 1H), 0.38-0.47 (m, 1H), 0.06-0.13 (m, 1H).

Workup

  1. custom” The product was obtained as an oil
  2. custom1H NMR (400 MHz, CDCl3) δ 7.73 and 7.47 (2 br s, total 1H), [7.49 (dd, J=5.8, 5.6 Hz) and 6.90 (dd, J=3.7, 3.6 Hz), total 1H], 6.99-7.09 (m, 1H), 5.87-5.93 (m, 1H), [4.54 (dd, half of ABX pattern, J=16.1, 3.6 Hz), 4.37 (dd, half of ABX pattern, J=16.0, 3.7 Hz), 4.28 (dd, half of ABX pattern, J=12.8, 5.5 Hz) and 4.14 (dd, half of ABX pattern, J=12.7, 5.8 Hz), total 2H], 3.74 and 3.74 (2 s, total 3H), 2.71-2.81 (m, 1H), 2.51-2.57 (m, 2H), 0.80-0.90 (m, 1H), 0.63-0.72 (m, 1H), 0.48-0.57 (m, 1H), 0.38-0.47 (m, 1H), 0.06-0.13 (m, 1H)

Sources & evidence

ORD record
ord-99d759abdbc7441abbec79c349b74e48
Source dataset
uspto-grants-2016_08
Patent number
US09403846B2

Reaction notes

Loading…