1,2-Dichloroethane → HCID 57889174, compound

HRID 1820284Notes

Reaction equation

HRID 1820284 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C@@H:13]([CH3:16])[CH2:14][CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([C@@:47]2([OH:55])[CH2:52][CH2:51][NH:50][CH2:49][C:48]2([CH3:54])[CH3:53])=[CH:43][CH:42]=1>C(Cl)(Cl)Cl.ClCCl>[Cl:40][C:41]1[CH:46]=[CH:45][C:44]([C@@:47]2([OH:55])[CH2:52][CH2:51][N:50]([C:10](=[O:12])[C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C@@H:13]([CH3:16])[CH2:14][CH3:15])[CH2:49][C:48]2([CH3:53])[CH3:54])=[CH:43][CH:42]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 83171N-[(1,1-Dimethylethoxy)carbonyl]-D-alloisoleucineHCID 18437142(S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol

Product 1

HCID 57889174HCID 57889174, compoundYield 86.6%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

(2R,3S)-2-(tert-butoxycarbonylamino)-3-methylpentanoic acid (197 mg, 0.85 mmol), EDC (162 mg, 0.85 mmol), HOBt (115 mg, 0.85 mmol) was dissolved in chloroform (10 mL). DIPEA (0.15 mL, 0.85 mmol) and (S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol (200 mg, 0.834 mmol) were added. The mixture was stirred at rt for 2 h, diluted with dichloromethane and washed with aq NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated to give tert-butyl (2R,3S)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxopentan-2-ylcarbamate (327 mg) as a yellow solid.

Workup

  1. washwashed with aq NaHCO3 and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-12d534e961cc4136bb8022327b81639d
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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