Sodium Azide → (2R)-2-(azidomethyl)-8-(2-chlorophenyl)-7-fluorochroman

HRID 902368Notes

Reaction equation

HRID 902368 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][CH:27]=[CH:26][C:25]=4[Cl:30])[C:17]([F:23])=[CH:18][CH:19]=3)[O:14]2)(=O)=O)=CC=1.[N-:31]=[N+:32]=[N-:33].[Na+]>CS(C)=O>[N:31]([CH2:12][C@H:13]1[CH2:22][CH2:21][C:20]2[C:15](=[C:16]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:30])[C:17]([F:23])=[CH:18][CH:19]=2)[O:14]1)=[N+:32]=[N-:33]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86609143((2R)-8-(2-chlorophenyl)-7-fluorochroman-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 86609144(2R)-2-(azidomethyl)-8-(2-chlorophenyl)-7-fluorochromanYield 67%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Treatment of ((2R)-8-(2-chlorophenyl)-7-fluorochroman-2-yl)methyl 4-methylbenzenesulfonate (0.7 g, 1.56 mmol) with sodium azide (0.61 g, 9.40 mmol) in DMSO (20 mL) according to the procedure described for Example 69, Step 9 provided 0.33 g (67%) of (2R)-2-(azidomethyl)-8-(2-chlorophenyl)-7-fluorochroman as a pale yellow oil.

Sources & evidence

ORD record
ord-9ff49f62874d4c1ea3c57239158f78dd
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

Loading…