Triethylamine → 7-(tert-butylamino-methyl)-6-chloro-chroman-4(S)-ol

HRID 747046Notes

Reaction equation

C1(C)C=CC(S(N[C@@H](C2C=CC=CC=2)[C@H](C2C=CC=CC=2)N)(=O)=O)=CC=1.CCN(CC)CC.[C:34]([NH:38][CH2:39][C:40]1[CH:49]=[C:48]2[C:43]([C:44](=[O:50])[CH2:45][CH2:46][O:47]2)=[CH:42][C:41]=1[Cl:51])([CH3:37])([CH3:36])[CH3:35]>CC(O)C.CC#N.CCCCCC.CCOCC>[C:34]([NH:38][CH2:39][C:40]1[CH:49]=[C:48]2[C:43]([C@@H:44]([OH:50])[CH2:45][CH2:46][O:47]2)=[CH:42][C:41]=1[Cl:51])([CH3:37])([CH3:35])[CH3:36]

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of (1S,2S)-(+)-N-(4-toluene-sulfonyl)-1,2-diphenylethylenediamine (0.29 g, 8.08 mmol) in i-PrOH (15 mL) was added [RuCl2(n6-p-cymene)]2, and Et3N under argon. The mixture was heated at 80° C. for 1 h, cooled, and concentrated to dryness. To this mixture was added a solution of 7-(tert-butylamino-methyl)-6-chloro-chroman-4-one (12 g, 44.91 mole) in anhydrous CH3CN (150 mL), followed by 5:2 formic acid/TEA (6 mL). The reaction was stirred at RT for 24 h. The mixture was concentrated, taken up in H2O, neutralized with 10% Na2CO3, extracted with CH2Cl2 (3×), dried over MgSO4, concentrated to give a brown foam which was stirred in hexane/ether (1:1), and filtered. The filtrate was concentrated to give a light brown foam.

Workup

temperaturecooled
concentrationconcentrated to dryness
concentrationThe mixture was concentrated
extractionextracted with CH2Cl2 (3×)
dry with materialdried over MgSO4
concentrationconcentrated
customto give a brown foam which
filtrationfiltered
concentrationThe filtrate was concentrated
customto give a light brown foam

Sources & evidence

ORD record: ord-fa808a2a741d4cb6b380f5d9f0d04208
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07393852B2

Reaction notes

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