Water → HCID 178453924, compound

HRID 72845Notes

Reaction equation

HRID 72845 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.CC(C[AlH]CC(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 14487Diisobutylaluminum hydrideHCID 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 1.2M solution of 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-9a7161474a364ec4bf7ff86c5cda9df1
Source dataset
uspto-grants-2014_09
Patent number
US08829029B2

Reaction notes

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