Toluene → HCID 68469873, compound

HRID 1875359Notes

Reaction equation

HRID 1875359 reaction equation
[O:1]=[C:2]1[CH2:8][N:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][C:4]2[S:14][CH:15]=[CH:16][C:3]1=2.C1(C)C=CC=CC=1>C(Cl)Cl>[OH:1][C@@H:2]1[CH2:8][N:7]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:6][CH2:5][C:4]2[S:14][CH:15]=[CH:16][C:3]1=2

Participants

4

Reactant 2

HCID 1140Toluene2×HCID 574239834-Oxo-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylic acid ethyl ester

Product 1

HCID 68469873HCID 68469873, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.86 g (16.1 mmol) ethyl 4-oxo-4,5,7,8-tetrahydro-thieno[2,3-d]azepine-6-carboxylate (prepared analogously to WO2007/84622) in 50 ml methylene chloride are combined, under argon, at −25° C., first with 1.92 ml of a 1.0 M toluene solution of (S)-3,3-diphenyl-1-methyl-tetrahydro-1H,3H-pyrrolo[1,2-c][1,3,2]oxazaborolidine and then with 20.2 ml of a 2 M borane-dimethylsulphide complex-toluene solution in 70 ml methylene chloride, and chilled to −18° C. for 3 days. Then sat. NH3Cl solution is added and the mixture is extracted 3× with methylene chloride. The combined organic phases are dried with NaSO4, concentrated and the crude product is purified by flash chromatography on silica gel (eluant DCM/methanol 95:5).

Workup

  1. additionThen sat. NH3Cl solution is added
  2. extractionthe mixture is extracted 3× with methylene chloride
  3. dry with materialThe combined organic phases are dried with NaSO4
  4. concentrationconcentrated
  5. customthe crude product is purified by flash chromatography on silica gel (eluant DCM/methanol 95:5)

Sources & evidence

ORD record
ord-89aaacd5a9f84747aabbf17bd0a049ef
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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