1,2-Dichloroethane → HCID 57889753, compound

HRID 1016134Notes

Reaction equation

HRID 1016134 reaction equation
[C:1]([NH:8][C@@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:16]([Cl:19])[CH2:17]Cl.[CH:20]1[CH:21]=CC2N(O)N=N[C:24]=2[CH:25]=1.CCN(C(C)C)C(C)C.[OH:39][CH:40]1[CH2:45][CH2:44][N:43](C2C=CC(Cl)=CC=2)[CH2:42][CH2:41]1>ClCCl>[Cl:19][C:16]1[CH:17]=[CH:24][C:25]([C:40]2([OH:39])[CH2:41][CH2:42][N:43]([C:13](=[O:15])[C@H:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:5])([CH3:6])[CH3:7])[CH:10]([CH3:11])[CH3:12])[CH2:44][CH2:45]2)=[CH:20][CH:21]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acidHCID 10727229HCID 10727229, compound

Product 1

HCID 57889753HCID 57889753, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Boc-D-valine (2.22 g, 10.2 mmol), EDC (1.96 g, 10.2 mmol), HOBt (1.38 g, 10.2 mmol) was dissolved in dichloromethane (40 mL). DIPEA (4.0 mL, 23.3 mmol) and 4-hydroxy-(4-chlorophenyl)piperidine (1.98 g, 9.34 mmol) was added and the solution was stirred at rt for 2 h. The reaction was concentrated and the resulting oily residue partitioned between EtOAc (150 mL) and water (50 mL), shaken and then separated. The organic layer was then washed with aq NaHCO3 (50 mL) and brine and the combined organic fractions were dried over solid sodium sulfate. The solution was filtered and concentrated by to give (R)-tert-butyl 1-(4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (3.9 g) as a white foam. MS found: (M+)+=411.1.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe resulting oily residue partitioned between EtOAc (150 mL) and water (50 mL)
  3. stirringshaken
  4. customseparated
  5. washThe organic layer was then washed with aq NaHCO3 (50 mL) and brine
  6. dry with materialthe combined organic fractions were dried over solid sodium sulfate
  7. filtrationThe solution was filtered
  8. concentrationconcentrated by

Sources & evidence

ORD record
ord-7e67f9552ef24222ad1d435b11c299e5
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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