Methylamine → (7-Benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(R)-ylmethyl)-methyl-amine

HRID 2221305Notes

Reaction equation

HRID 2221305 reaction equation
[CH3:1][NH2:2].[C:3]1([S:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:20][CH2:19][C@@H:18]([CH2:21]OS(C)(=O)=O)[O:17][C:16]=3[CH:27]=2)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[C:3]1([S:9]([C:12]2[CH:13]=[CH:14][C:15]3[O:20][CH2:19][C@@H:18]([CH2:21][NH:2][CH3:1])[O:17][C:16]=3[CH:27]=2)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 59710884methansulfonic acid 7-benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(S)-yl-methyl ester

Product 1

HCID 11652654(7-Benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(R)-ylmethyl)-methyl-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2M solution of methyl amine in methanol (10 mL) and methansulfonic acid 7-benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(S)-yl-methyl ester (0.87 g, 2.26 mmol) were heated in a microwave at 100° C. for 3 hours. The solvent was removed under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluting with dichloromethane—methanol; 98:2, v/v) to give (7-Benzenesulfonyl-2,3-dihydro-benzo[1,4]dioxin-2(R)-ylmethyl)-methyl-amine as a white solid (0.557 g; 77%), which was converted to a hydrochloride salt: MS (M)+ 319; m. p. 240.0-243.6° C., [α]=+40.5° (methanol; c=1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe crude material was purified by flash chromatography on silica gel (
  3. washeluting with dichloromethane—methanol

Sources & evidence

ORD record
ord-ef3a781b95f14b328e9c00c17425e6b1
Source dataset
uspto-grants-2008_05
Patent number
US07368567B2

Reaction notes

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