Diisobutylaluminum hydride → HCID 86650840, compound

HRID 1424616Notes

Reaction equation

HRID 1424616 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:28]=1[C:9]1([CH2:14][CH2:13][N:12]([C:15](=[O:27])[NH:16][CH:17]3[CH:24]4[CH2:25][CH:20]5[CH2:21][CH:22]([CH2:26][CH:18]3[CH2:19]5)[CH2:23]4)[CH2:11][CH2:10]1)[CH2:8][CH:7]2[C:29]([CH3:36])([CH3:35])[C:30](OCC)=[O:31].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:28]=1[C:9]1([CH2:10][CH2:11][N:12]([C:15]([NH:16][CH:17]3[CH:24]4[CH2:25][CH:20]5[CH2:21][CH:22]([CH2:26][CH:18]3[CH2:19]5)[CH2:23]4)=[O:27])[CH2:13][CH2:14]1)[CH2:8][CH:7]2[C:29]([CH3:36])([CH3:35])[CH:30]=[O:31]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86650841HCID 86650841, compound

Product 1

HCID 86650840HCID 86650840, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of (±)-ethyl 2-(7-bromo-1′-((2-adamantyl)carbamoyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)-2-methylpropanoate (100 mg, 0.18 mmol) in anhydrous toluene was added DIBAL-H (0.4 mL, 1 M) at −78° C. The mixture was stirred for 30 min and quenched with MeOH. The organic layer was separated, dried and concentrated to give crude (±)-7-bromo-N-(2-adamantyl)-3-(2-methyl-1-oxopropan-2-yl)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxamide which was used for the next step without purification.

Workup

  1. customquenched with MeOH
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e582f839a32e4c958beec2f37909fbf9
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

Loading…