Ammonia → [(2S)-5-Fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methylamine

HRID 39035Notes

Reaction equation

HRID 39035 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:18][C:17]3[CH:19]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:21]=[C:22]([F:23])[C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[NH3:28]>>[F:23][C:22]1[C:16]2[O:15][CH2:14][C@H:13]([CH2:12][NH2:28])[O:18][C:17]=2[CH:19]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:21]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 86652937[(2R)-5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate

Product 1

HCID 67198473[(2S)-5-Fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methylamine

Conditions

Temperature
120 °C

Procedure

A mixture of [(2R)-5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.7 g, 1.7 mmol), NH3 (6 ml, 7N in methanol) was heated under microwave radiation at 120° C. for 20 min. The product was evaporated to dryness and was purified on an SCX-3 column (TEA/MeOH) Yield 0.34 g. MS m/z (rel. intensity, 70 eV) 261 (M+, bp), 217 (49), 97 (39), 69 (55), 56 (79).

Workup

  1. customThe product was evaporated to dryness
  2. customwas purified on an SCX-3 column (TEA/MeOH) Yield 0.34 g

Sources & evidence

ORD record
ord-0ecd56fbc85842d2b8aad7006a6ce224
Source dataset
uspto-grants-2013_09
Patent number
US08524766B2

Reaction notes

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