Lithium borohydride → HCID 178527344, compound

HRID 2354883Notes

Reaction equation

HRID 2354883 reaction equation
[BH4-].[Li+].C([O:5][C:6]([CH:8]1[CH2:18][CH:17]2[N:19]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:10]([CH2:11][C:12]3[NH:13][N:14]=[CH:15][C:16]=32)[CH2:9]1)=O)C>C1COCC1>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([S:20]([N:19]2[CH:10]3[CH2:9][CH:8]([CH2:6][OH:5])[CH2:18][CH:17]2[C:16]2[C:12]([CH2:11]3)=[N:13][NH:14][CH:15]=2)(=[O:22])=[O:21])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 16045395HCID 16045395, compound

Product 1

HCID 178527344HCID 178527344, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium borohydride (17 mg, 0.80 mmol) was added to a solution of 12-(4-chloro-benzenesulfonyl)-4,5,12-triaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene-10-carboxylic acid ethyl ester (328 mg, 0.80 mmol) in THF (3 mL). The resulting solution was stirred at room temperature for 18 h then heated to 60° C. for 2 h. The reaction was quenched by the addition of water (5 mL) and the resulting mixture was extracted with EtOAc (3×5 mL). The combined organic phases were dried (Na2SO4), filtered, concentrated and purified by silica gel column chromatography (eluant hexane/EtOAc, 9/1 to 1/1) and preparative HPLC to give [12-(4-chloro-benzenesulfonyl)-4,5,12-triaza-tricyclo[6.3.1.02,6]dodeca-2,5-dien-10-yl]-methanol as a white solid. Retention time (min)=1.242, method [1], MS (ESI) 368.0 (M+H); 1H NMR (300 MHz, CDCl3) δ 7.73 (d, J=8.2 Hz, 2H), 7.58 (s, 1H), 7.38 (d, J=8.2 Hz, 2H), 5.33 (s, 1H), 4.48 (d, J=7.1 Hz, 1H), 3.41 (d, J=2.7 Hz, 2H), 3.08 (dd, J=17.6, 7.7 Hz, 1H), 2.62 (d, J=17.6 Hz, 1H), 1.81-1.54 (m, 5H).

Workup

  1. temperaturethen heated to 60° C. for 2 h
  2. customThe reaction was quenched by the addition of water (5 mL)
  3. extractionthe resulting mixture was extracted with EtOAc (3×5 mL)
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica gel column chromatography (eluant hexane/EtOAc, 9/1 to 1/1) and preparative HPLC

Sources & evidence

ORD record
ord-84ea650fe8ca4ff7a9f5ee203b4c7898
Source dataset
uspto-grants-2010_07
Patent number
US07754712B2

Reaction notes

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