Dimethyl Sulfide → HCID 59383025, compound

HRID 2355456Notes

Reaction equation

HRID 2355456 reaction equation
[F:1][C:2]([F:24])([F:23])[CH2:3][NH:4][C:5]([C@@H:7]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=O.S(C)C>C1COCC1>[F:1][C:2]([F:23])([F:24])[CH2:3][NH:4][CH2:5][C@@H:7]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:19])[CH3:20])[CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 59382986HCID 59382986, compound

Product 1

HCID 59383025HCID 59383025, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (S)-1-(2,2,2-trifluoroethylcarbamoyl)-2-cyclohexylethyl-carbamate (1.8 g, 5.1 mmol) in anhydrous THF (30 mL) was added 2 M BH3.Me2S in THF (25 mL, 50 mmol) and the mixture was stirred at rt for 3 d. The reaction was quenched with MeOH (20 mL), the solvent was removed in vacuo and the residue was purified by silica chromatography to give crude tert-butyl (S)-1-(2,2,2-trifluoroethylamino)-3-cyclohexylpropan-2-ylcarbamate (1.7 g).

Workup

  1. customThe reaction was quenched with MeOH (20 mL)
  2. customthe solvent was removed in vacuo
  3. customthe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-bdd9c58289a048e6bcd1d8914abc0597
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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