Thiophenol → HCID 60664686, compound

HRID 1881051Notes

Reaction equation

HRID 1881051 reaction equation
C(OC(=O)[N:7]([CH2:15][CH2:16]O)[C@H:8]1[CH2:13][CH2:12][C@H:11]([CH3:14])[CH2:10][CH2:9]1)(C)(C)C.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:50]1([SH:56])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1>C1COCC1>[CH3:14][CH:11]1[CH2:10][CH2:9][CH:8]([NH:7][CH2:15][CH2:16][S:56][C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 7969Thiophenol2×HCID 11776Triphenylphosphine2×HCID 5462977Diethyl azodicarboxylate2×HCID 178453761HCID 178453761, compound

Product 1

HCID 60664686HCID 60664686, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2-Hydroxy-ethyl)-(trans-4-methyl-cyclohexyl)-carbamic acid tert-butyl ester (0.50 g, 1.94 mmol) in THF (20 mL) was added DEAD (372 mg, 2.14 mmol) and resin bound triphenyl phosphine (polystyrene 2% cross linking, loading=3 mmol/g, 0.97 g). The mixture was stirred for 15 m before thiophenol (0.21 g, 1.94 mmol) was added. The mixture was stirred for 18 h before another portion of resin bound triphenyl phosphine (0.97 g) and DEAD (372 mg, 2.14 mmol) was added. The mixture was stirred for 1 h before a new portion of thiophenol (0.21 g, 1.94 mmol) was added. The mixture was stirred for 18 h before it was filtered. The resin was washed with THF (2×20 mL) and the combined filtrates were concentrated in vacuo. The residue was divided between DCM (100 mL) and H2O (100 mL). The aqueous layer was extracted once more with DCM (100 mL). The organic fractions were combined, dried (MgSO4), filtered and concentrated in vacuo to give the crude intermediate (4-methyl-cyclohexyl)-(2-phenylsulfanyl-ethyl)-amine.

Workup

  1. additionwas added
  2. additionwas added
  3. additionwas added
  4. stirringThe mixture was stirred for 18 h before it
  5. filtrationwas filtered
  6. washThe resin was washed with THF (2×20 mL)
  7. concentrationthe combined filtrates were concentrated in vacuo
  8. extractionThe aqueous layer was extracted once more with DCM (100 mL)
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cb88e028f4a94ea4a2352b751107fbb1
Source dataset
uspto-grants-2012_11
Patent number
US08318778B2

Reaction notes

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