Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate → 5-(5-Chloro-7-morpholin-4-yl-thiazolo[5,4-d]pyrimidin-2-ylmethyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester

HRID 1919371Notes

Reaction equation

HRID 1919371 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[N:10]=[C:9]([CH:11]=O)[S:8][C:6]=2[N:7]=1.[C:19]([O:23][C:24]([N:26]1[CH2:33][CH:32]2[CH:28]([CH2:29][NH:30][CH2:31]2)[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:19]([O:23][C:24]([N:26]1[CH2:27][CH:28]2[CH:32]([CH2:31][N:30]([CH2:11][C:9]3[S:8][C:6]4[N:7]=[C:2]([Cl:1])[N:3]=[C:4]([N:13]5[CH2:18][CH2:17][O:16][CH2:15][CH2:14]5)[C:5]=4[N:10]=3)[CH2:29]2)[CH2:33]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 576854055-Chloro-7-morpholinothiazolo[5,4-d]pyrimidine-2-carbaldehyde

Product 1

HCID 582349385-(5-Chloro-7-morpholin-4-yl-thiazolo[5,4-d]pyrimidin-2-ylmethyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl esterYield 86.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 5-chloro-7-morpholin-4-yl-thiazolo[5,4-d]pyrimidine-2-carbaldehyde (57 mg, 0.20 mmol) in 1,2-dichloroethane (2 mL) was added hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylic acid tert-butyl ester (46 mg, 0.22 mmol). The mixture was stirred at RT for 5 min before sodium triacetoxyborohydride (64 mg, 0.30 mmol) was added. The resulting solution was stirred at RT for 1 h. The crude reaction mixture was partitioned between DCM and brine. The organic layer was isolated, then dried (MgSO4) and concentrated in vacuo. The resultant residue was purified by column chromatography to give the title compound as a white solid (83 mg, 86%).

Workup

  1. additionwas added
  2. customThe crude reaction mixture
  3. customwas partitioned between DCM and brine
  4. customThe organic layer was isolated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-5daa7d35c0914f90aa90e6f2f6c74a93
Source dataset
uspto-grants-2012_05
Patent number
US08168633B2

Reaction notes

Loading…