Diisobutylaluminum hydride → HCID 68678691, compound

HRID 1444734Notes

Reaction equation

HRID 1444734 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]=[CH:5][N:4]([S:8]([C:11]2[CH:17]=[CH:16][C:14]([CH3:15])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:3]1[CH2:18][C:19]([N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C@@H:22]1[C:27]1[CH:36]=[CH:35][C:30]([C:31](OC)=[O:32])=[CH:29][CH:28]=1)=[O:20].CC(C[AlH]CC(C)C)C>C(Cl)Cl>[OH:32][CH2:31][C:30]1[CH:29]=[CH:28][C:27]([CH:22]2[CH2:23][CH2:24][CH2:25][CH2:26][N:21]2[C:19](=[O:20])[CH2:18][C@H:3]2[N:4]([S:8]([C:11]3[CH:12]=[CH:13][C:14]([CH3:15])=[CH:16][CH:17]=3)(=[O:10])=[O:9])[CH:5]=[CH:6][NH:7][C:2]2=[O:1])=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 68681229HCID 68681229, compound

Product 1

HCID 68678691HCID 68678691, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-methyl 4-(1-(2-(3-oxo-1-tosyl-1,2,3,4-tetrahydropyrazin-2-yl)acetyl)piperidin-2-yl)benzoate (0.562 g, 1.10 mmol) in CH2Cl2 stirred in dryice-acetone bath under N2 was added DIBAL (1.0M solution in CH2Cl2, 5.50 ml, 5.50 mmol) via syringe over 15 min, and stirred for 30 min. The cold bath was removed and after 2 h MeOH (6.0 ml) was added followed by Na2SO4 (12.0 g) and sat'd NH4Cl aq. (0.30 ml). After 30 min the mixture was filtered and the filtercake was washed with CH2Cl2/MeOH (10/1). The filtrate was concentrated under reduced pressure and the residue was chomatographed on silica (CH2Cl2→CH2Cl2/MeOH=20/1) to yield the product. MS 482.2 (M+H).

Workup

  1. customThe cold bath was removed and after 2 h MeOH (6.0 ml)
  2. additionwas added
  3. filtrationAfter 30 min the mixture was filtered
  4. washthe filtercake was washed with CH2Cl2/MeOH (10/1)
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto yield the product

Sources & evidence

ORD record
ord-935775b697384682b40b3c09fd89e3e2
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

Loading…