tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate → HCID 58247418, compound

HRID 1894157Notes

Reaction equation

HRID 1894157 reaction equation
[CH2:1]([O:8][C:9](=[O:31])[NH:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][C:18]2[C:23]([NH2:24])=[CH:22][N:21]=[C:20]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[N:19]=2)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32]([N:39]1[CH2:45][CH2:44][CH2:43][C@H:40]1[CH:41]=O)([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.O>[C:35]([O:34][C:32]([N:39]1[CH2:45][CH2:44][CH2:43][C@H:40]1[CH2:41][NH:24][C:23]1[C:18]([O:17][C:14]2[CH:13]=[CH:12][C:11]([NH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:31])=[CH:16][CH:15]=2)=[N:19][C:20]([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)=[N:21][CH:22]=1)=[O:33])([CH3:38])([CH3:36])[CH3:37]

Participants

6

Reactant 3

HCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 58247431[4-(5-Amino-2-pyridin-3-yl-pyrimidin-4-yloxy)-phenyl]-carbamic acid benzyl ester

Product 1

HCID 58247418HCID 58247418, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a solution of Compound 11b (0.55 g; 1.3 mmol) in 1,2-dichloroethane (25 ml) was added Boc-L-prolinal (0.37 mL; 1.9 mmol). To the reaction mixture was then added NaBH(OAc)3 (0.4 g; 1.9 mmol) portionwise, and the reaction mixture was continually stirred at room temperature for 5 h. The resultant mixture was diluted with water. After stirring for 10 min the organic phase was isolated, washed with brine, and dried over MgSO4. The solvent was evaporated in vacuo to afford Compound 11c. The compound was used in the next step without further purification.

Workup

  1. customwas isolated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-cc9faf85365e4fad9326f2f2a5736e92
Source dataset
uspto-grants-2013_08
Patent number
US08513271B2

Reaction notes

Loading…