Sodium Azide → HCID 14352643, compound

HRID 1088026Notes

Reaction equation

S([O-])(=O)(=O)C.[N-]=[N+]=[N-].[Na+].[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][CH2:17][CH2:18][C@@H:19]1[C@H:24]([N:25]=[N+:26]=[N-:27])[CH2:23][C@H:22]2[CH2:28][C@@H:20]1[C:21]2([CH3:30])[CH3:29]>>[O:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[O:16][CH2:17][CH2:18][C@H:19]1[C@H:24]([N:25]=[N+:26]=[N-:27])[CH2:23][C@H:22]2[CH2:28][C@@H:20]1[C:21]2([CH3:30])[CH3:29]

Participants

Reactant 3

HCID 33557Sodium Azide

HCID 85257Methanesulfonate

HCID 14352641HCID 14352641, compound

Product 1

HCID 14352643HCID 14352643, compound

Procedure

Diethyl azadicarboxylate (20 g) was added dropwise to a suspension of the alcohol 1(2R-c) (6.11 g), triphenylphosphin (30 g) and zinc dimethanesulfonate (5.83 g) in benzene (350 ml) at room temperature under nitrogen. The mixture was stirred at room temperature for 3 h, washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel in hexane ethyl acetate (5:1) to give the crude mesylate (6.7 g). The mesylate was treated with sodium azide by the same procedure cited for the preparation of 15 (IV-2, Example 2 (2)), 2.05 g, 31.3%. nmr δ (CDCl3) 0.86 (3H, s), 1.21 (3H, s),1.28 (1H, d, J=10 Hz), 1.40-2.50 (14H), 3.22-4.00 (5H), 4.57 (1H, m).

Sources & evidence

ORD record: ord-2986a29b43c04fc78dae4959286e2804
Source dataset: uspto-grants-1990_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04960909

Reaction notes

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