Sodium Azide → HCID 86609148, compound

HRID 902377Notes

Reaction equation

HRID 902377 reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:22][CH2:21][C:20]3[C:15](=[C:16]([C:24]4[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=4[CH3:31])[C:17]([F:23])=[CH:18][CH:19]=3)[O:14]2)(=O)=O)=CC=1.[N-:32]=[N+:33]=[N-:34].[Na+]>CS(C)=O>[N:32]([CH2:12][C@H:13]1[CH2:22][CH2:21][C:20]2[C:15](=[C:16]([C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=3[CH3:31])[C:17]([F:23])=[CH:18][CH:19]=2)[O:14]1)=[N+:33]=[N-:34]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86609147HCID 86609147, compound

Product 1

HCID 86609148HCID 86609148, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Treatment of ((2R)-8-(4-chloro-2-methylphenyl)-7-fluorochroman-2-yl)methyl 4-methylbenzenesulfonate (0.5 g, 1.09 mmol) with sodium azide (0.43 g, 6.54 mmol) in DMSO (15 mL) according to the procedure described for Example 69, Step 9 provided 0.30 g (83%) of (2R)-2-(azidomethyl)-8-(4-chloro-2-methylphenyl)-7-fluorochroman as a colorless oil.

Sources & evidence

ORD record
ord-3ffce8444efe4422b98850c7c1663bd8
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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