Sodium Azide → (2R)-2-(azidomethyl)-8-(biphenyl-2-yl)-6-fluorochroman

HRID 902395Notes

Reaction equation

HRID 902395 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[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)[CH:17]=[C:18]([F:23])[CH:19]=3)[O:14]2)(=O)=O)=CC=1.[N-:36]=[N+:37]=[N-:38].[Na+]>CS(C)=O>[N:36]([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[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:17]=[C:18]([F:23])[CH:19]=2)[O:14]1)=[N+:37]=[N-:38]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86609155((2R)-8-(biphenyl-2-yl)-6-fluorochroman-2-yl)methyl 4-methylbenzenesulfonate

Product 1

HCID 86609156(2R)-2-(azidomethyl)-8-(biphenyl-2-yl)-6-fluorochromanYield 89%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Treatment of ((2R)-8-(biphenyl-2-yl)-6-fluorochroman-2-yl)methyl 4-methylbenzenesulfonate (1.30 g, 2.66 mmol) with sodium azide (1.04 g, 15.96 mmol) in DMSO (30 mL) according to the procedure described for Example 69, Step 9 provided 0.85 g (89%) of (2R)-2-(azidomethyl)-8-(biphenyl-2-yl)-6-fluorochroman as a pale yellow oil.

Sources & evidence

ORD record
ord-8f8449d3af9c4feea6155572621f90e1
Source dataset
uspto-grants-2008_04
Patent number
US07365095B2

Reaction notes

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