(Dimethyl sulfide)trihydroboron → HCID 86756029, compound

HRID 1937468Notes

Reaction equation

HRID 1937468 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:25][CH3:26])=[C:13]([C:16]3([C:21](OC)=[O:22])[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:14]=2)[C@H:9]([N:27]([CH2:32][C:33]2[CH:38]=[C:37]([C:39]([F:42])([F:41])[F:40])[CH:36]=[C:35]([C:43]([F:46])([F:45])[F:44])[CH:34]=2)[C:28]([O:30][CH3:31])=[O:29])[CH2:8][C@@H:7]1[CH3:47])=[O:5])[CH3:2].B.CSC>O1CCCC1>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:25][CH3:26])=[C:13]([C:16]3([CH2:21][OH:22])[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:14]=2)[C@H:9]([N:27]([CH2:32][C:33]2[CH:38]=[C:37]([C:39]([F:40])([F:41])[F:42])[CH:36]=[C:35]([C:43]([F:45])([F:44])[F:46])[CH:34]=2)[C:28]([O:30][CH3:31])=[O:29])[CH2:8][C@@H:7]1[CH3:47])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 86756030HCID 86756030, compound

Product 1

HCID 86756029HCID 86756029, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6-methoxy-7-(1-methoxycarbonyl-cyclopentyl)-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 27) (700 mg; 1.04 mmol) in 20 mL anhydrous tetrahydrofuran was added borane-dimethylsulfide complex (1M THF; 2.28 mL) and the reaction was heated to reflux for 3 hours. The reaction was quenched with H2O and extracted with 50 mL of ethyl acetate. The organic phase was dried (MgSO4), filtered and concentrated. The residue was chromatographed (25% ethyl acetate-hexane) to afford the title product (20 mg). MS m/z 664 (M++18); 1H NMR (CDCl3) δ 1.1 (d, 3H), 3.6 (s, 2H), 3.7 (s, 3H), 3.8 (s, 3H), 6.3 (S, 1H), 7.3 (S, 1H), 7.7 (S, 2H), 7.8 (S, 1H).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 3 hours
  3. customThe reaction was quenched with H2O
  4. extractionextracted with 50 mL of ethyl acetate
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was chromatographed (25% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-eb6be4abee3a4d38bc10adb84f42528f
Source dataset
uspto-grants-2002_05
Patent number
US06395751B1

Reaction notes

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