Toluene → HCID 66842550, compound

HRID 875269Notes

Reaction equation

HRID 875269 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]2[C:19](=[O:20])[O:18][C@H:17]3[C:21]4[C@@:26]([CH3:29])([CH2:27][CH2:28][C:16]23[OH:31])[CH2:25][CH2:24][CH2:23][C:22]=4[CH3:30])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.CC(C[AlH]CC(C)C)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]2[CH:19]([OH:20])[O:18][C@H:17]3[C:21]4[C@@:26]([CH3:29])([CH2:27][CH2:28][C:16]23[OH:31])[CH2:25][CH2:24][CH2:23][C:22]=4[CH3:30])[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 14487Diisobutylaluminum hydrideHCID 24436Sodium SulfateHCID 42599313HCID 42599313, compound

Product 1

HCID 66842550HCID 66842550, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound of example 27 (200 mg, 0.47 mmol) was dissolved in anhydrous DCM and toluene (1:1) (2 mL) and solution was cooled to −78° C. DIBAL in toluene (1.0 M, 1.4 mL, 1.2 equivalents) was added dropwise at −78° C. and mixture was stirred for 3 hours. Saturated sodium sulphate solution was added and reaction mixture was extracted by DCM (3×50 mL), dried over sodium sulphate and was concentrated to obtain the title compound.

Workup

  1. customreaction mixture
  2. extractionwas extracted by DCM (3×50 mL)
  3. dry with materialdried over sodium sulphate
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-20fc3580e82b4db5855e2df504eccfe3
Source dataset
uspto-grants-2015_03
Patent number
US08981131B2

Reaction notes

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