HCID 70558534, compound → HCID 70556450, compound

HRID 707681Notes

Reaction equation

HRID 707681 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@:9]12[CH2:16][O:15][C@H:14]([CH2:17][O:18][C:19]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C@H:13]1[CH2:12][O:11][NH:10]2>C(O)(=O)C.[Zn]>[NH2:10][C@@:9]1([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([F:8])[C:2]=2[F:1])[CH2:16][O:15][C@H:14]([CH2:17][O:18][C:19]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C@H:13]1[CH2:12][OH:11]

Participants

4

Reactant 1

HCID 70558534HCID 70558534, compound

Product 1

HCID 70556450HCID 70556450, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc powder (20.0 g) was added to a solution containing (3aR,4S,6aS)-6a-(2,3-difluorophenyl)-4-((trityloxy)methyl)hexahydrofuro[3,4-c]isoxazole, obtained in Preparation Example 1-(2), (15.51 g) in acetic acid (120 mL) at 0° C. The reaction solution was allowed to warm to RT and stirred for 18 h. The insoluble matter was separated by filtration through Celite®, washing with acetic acid (100 mL) and AcOEt (300 mL), and the filtrate was concentrated. Saturated aqueous NaHCO3 solution was added carefully to neutralize the residue, and the mixture was extracted with EtOAc (3×200 mL). The combined organic layers were dried over MgSO4 and evaporated to obtain the title compound (15.42 g). 1H-NMR (400 MHz, CDCl3) δ (ppm): 2.60-2.68 (m, 1H), 2.85 (br s, 3H), 3.29 (d, J=4.8 Hz, 2H), 3.66 (dd, J=12.1, 4.8 Hz, 1H), 3.89-3.99 (m, 2H), 4.31 (d, J=9.1 Hz, 1H), 4.34-4.40 (m, 1H), 7.04-7.19 (m, 2H), 7.20-7.33 (m, 10H), 7.39-7.50 (m, 6H)

Workup

  1. customat 0° C
  2. customThe insoluble matter was separated by filtration through Celite®
  3. washwashing with acetic acid (100 mL) and AcOEt (300 mL)
  4. concentrationthe filtrate was concentrated
  5. additionSaturated aqueous NaHCO3 solution was added carefully
  6. extractionthe mixture was extracted with EtOAc (3×200 mL)
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-21d912a09d2a4496ba3885fe59e240a7
Source dataset
uspto-grants-2015_11
Patent number
US09175013B2

Reaction notes

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