Sodium Azide → HCID 86667162, compound

HRID 2367936Notes

Reaction equation

HRID 2367936 reaction equation
[C:1]1([C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:8][C@@H:9]2[CH2:15][CH2:14][CH2:13][C@@H:12]3[C@H:10]2[O:11]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:28]=[N+:29]=[N-:30].[Na+]>O.CO.C(Cl)Cl>[N:28]([C@H:12]1[CH2:13][CH2:14][CH2:15][C@@H:9]([O:8][C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C@@H:10]1[OH:11])=[N+:29]=[N-:30]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 86667163HCID 86667163, compound

Product 1

HCID 86667162HCID 86667162, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

The diastereomeric mixture of (1R,2R,6R)-2-(triphenylmethoxy)-7-oxabicyclo[4.1.0]heptane 1 (755 mg, 2.12 mmol) and the S,S-epoxide was dissolved with NaN3 (861 mg, 13.3 mmol) in H2O (1.7 mL) and MeOH (15 mL). The mixture was heated to 80° C., refluxed over night and then diluted with water and CH2Cl2. The organic layer was separated and the aqueous layer was rewashed (CH2Cl2). The entire organic layer was dried (MgSO4), filtered and concentrated. Purification was made by recrystallization in MeOH at −18° C. The reaction yielded 62% of 2. 1H-NMR (CDCl3) 7.50 (m, 6 H), 7.20-7.40 (m, 9 H), 3.69 (t, J=9.50 Hz, 1 H), 3.05 (ddd, J=4.80, 9.44, 12.05 Hz, 1 H), 2.91 (ddd, J=4.17, 8.81, 11.28 Hz, 1 H), 2.70 (s, 1 H), 1.80 (m, 1 H), 1.50 (m, 2 H), 1.20-1.40 (m, 2 H), 0.80 (m, 1 H).

Workup

  1. temperaturerefluxed over night
  2. customThe organic layer was separated
  3. dry with materialThe entire organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification
  7. customwas made by recrystallization in MeOH at −18° C

Sources & evidence

ORD record
ord-ff27ab4b13054f5681a528daca64fb06
Source dataset
uspto-grants-2014_04
Patent number
US08703720B2

Reaction notes

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