Potassium tert-butoxide → 4a-(4-Chloro-benzenesulfonyl)-5,8-difluoro-2,3,4,4a,10,10a-hexahydro-1H-9-oxa-1-aza-phenanthrene

HRID 564326Notes

Reaction equation

HRID 564326 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[C:20]3[C:15](=[C:16]([F:22])[CH:17]=[CH:18][C:19]=3[F:21])[O:14][CH2:13][CH:12]2[NH:23][CH2:24][CH2:25][CH2:26]OS(C)(=O)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]23[C:20]4[C:15](=[C:16]([F:22])[CH:17]=[CH:18][C:19]=4[F:21])[O:14][CH2:13][CH:12]2[NH:23][CH2:24][CH2:25][CH2:26]3)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 72472619HCID 72472619, compound

Product 1

HCID 670064054a-(4-Chloro-benzenesulfonyl)-5,8-difluoro-2,3,4,4a,10,10a-hexahydro-1H-9-oxa-1-aza-phenanthrene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonic acid 3-[4-(4-chloro-benzenesulfonyl)-5,8-difluoro-chroman-3-ylamino]-propyl ester (0.28 g, 0.57 mmol) was dissolved in 25 ml of tetrahydrofuran then 1 M potassium tert-butoxide solution (2.40 ml, 2.40 mmol) was added. The reaction was stirred at room temperature for 3.5 h. The reaction was quenched with 50 ml of water and washed with 50 ml of ethyl acetate. The organic layer was dried over Na2SO4 and concentrated. The product was purified by prep TLC (EtOAc/Hex. 50/50). Yield: 140 mg, 60%. 1H NMR (CDCl3 400 MHz) δ 7.60 (d, J=8.1 Hz, 2H), 7.49 (d, J=8.8 Hz, 2H), 7.08 (td, J=9.5, 4.4 Hz, 1H), 6.47-6.40 (m, 1H), 5.21 (dd, J=11.8, 2.2 Hz, 1H), 4.33 (d, J=11.8 Hz, 1H), 3.70 (s, 1H), 3.00 (d, J=13.2 Hz, 1H), 2.76 (td, J=12.4 Hz, 2.9 Hz, 1H), 2.68 (d, J=13.2 Hz, 1H), 2.17 (tt, J=13.2, 2.9 Hz 1H), 1.66-1.44 (m, 2H), 1.21-1.07 (m, 1H).

Workup

  1. customThe reaction was quenched with 50 ml of water
  2. washwashed with 50 ml of ethyl acetate
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated
  5. customThe product was purified by prep TLC (EtOAc/Hex. 50/50)

Sources & evidence

ORD record
ord-e94ddc6bf7664ea19b00516d7f5901e3
Source dataset
uspto-grants-2011_11
Patent number
US08067621B2

Reaction notes

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