Water → HCID 178453924, compound

HRID 1714388Notes

Reaction equation

HRID 1714388 reaction equation
C([O:3][C:4](=O)[CH2:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8][CH2:7]1)C.[H-].C([Al+]CC(C)C)C(C)C.O>C1(C)C=CC=CC=1>[C:16]([O:15][C:13](=[O:14])[NH:12][C@H:9]1[CH2:8][CH2:7][C@H:6]([CH2:5][CH:4]=[O:3])[CH2:11][CH2:10]1)([CH3:19])([CH3:17])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 21225700DiisobutylaluminumhydrideHCID 178471811HCID 178471811, compound

Product 1

HCID 178453924HCID 178453924, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of trans-(4-tert-butoxycarbonylamino-cyclohexyl)-acetic acid ethyl ester (1.04 g, 4 mmol), in toluene (10 mL) at −78° C. a 1.2 M solution of diisobutylaluminium hydride (DIBAL-H) (5.1 mL, 6 mmol) in toluene was added. The mixture was stirred at −78° C. until TLC after 0.5 h indicated completion of the reaction. Water was added and the solution was extracted three times with dichloromethane. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered and evaporated. The crude product was used without purification on the next step. MS (m/e): 242.3 (M+H+).

Workup

  1. customcompletion of the reaction
  2. extractionthe solution was extracted three times with dichloromethane
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was used without purification on the next step

Sources & evidence

ORD record
ord-2f5d81d1c5524c85a0843c3a8edf617b
Source dataset
uspto-grants-2010_09
Patent number
US07795437B2

Reaction notes

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