Diisobutylaluminum hydride → HCID 18436347, compound

HRID 351452Notes

Reaction equation

HRID 351452 reaction equation
C([O:3][C:4]([CH:6]1[CH:11]([CH3:12])[CH:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:16][CH:15]=2)[C:9]([C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=2)=[CH:8][CH2:7]1)=O)C.CC(C[AlH]CC(C)C)C>C(Cl)Cl>[OH:3][CH2:4][C:6]1[CH:11]([CH3:12])[CH:10]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)=[CH:16][CH:15]=2)[CH:9]([C:29]2[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=2)[CH2:8][CH:7]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 69423712HCID 69423712, compound

Product 1

HCID 18436347HCID 18436347, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-(4-Hydroxy-phenyl)-6-methyl-5-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-cyclohex-3-enecarboxylic acid ethyl ester (38.4 mg, 0.0803 mmol, 1.0 eq.) in DCM (2 mL) at 0° C. was added DIBAL (1.5 M in toluene, 0.215 mL) and was stirred at 0° C. for 10 min, then at 25° C. for 30 min. The reaction mixture was quenched at 0° C. with brine, extracted with DCM, dried over MgSO4, then purified on SiO2 (15% MeOH/DCM) to yield 4-[4-hydroxymethyl-5-methyl-6-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-cyclohex-3-enyl]-phenol as yellowish foam.

Workup

  1. waitat 25° C. for 30 min
  2. customThe reaction mixture was quenched at 0° C. with brine
  3. extractionextracted with DCM
  4. dry with materialdried over MgSO4
  5. custompurified on SiO2 (15% MeOH/DCM)

Sources & evidence

ORD record
ord-61e1b5b3303248cfadcd1987f6b3fb62
Source dataset
uspto-grants-2007_02
Patent number
US07183445B2

Reaction notes

Loading…