Sodium triacetoxyborohydride → (3R)-3-({1-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl](4-piperidyl)}amino)-1-(4-chlorophenyl)pyrrolidin-2-one

HRID 271253Notes

Reaction equation

HRID 271253 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[C:3]1=[O:14].[OH:15][C@@H:16]([CH2:25][O:26][C:27]1[CH:28]=[CH:29][C:30]2[S:34][C:33]([CH3:35])=[N:32][C:31]=2[CH:36]=1)[CH2:17][N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CCO>[OH:15][C@@H:16]([CH2:25][O:26][C:27]1[CH:28]=[CH:29][C:30]2[S:34][C:33]([CH3:35])=[N:32][C:31]=2[CH:36]=1)[CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([NH:1][C@@H:2]2[CH2:6][CH2:5][N:4]([C:7]3[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=3)[C:3]2=[O:14])[CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 587143351-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperidin-4-oneHCID 58714338(3R)-3-amino-1-(4-chlorophenyl)pyrrolidin-2-one

Product 1

HCID 58714334(3R)-3-({1-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl](4-piperidyl)}amino)-1-(4-chlorophenyl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3R)-3-amino-1-(4-chlorophenyl)pyrrolidin-2-one as prepared in Example 14 (0.08 g) in EtOH (3 ml) was added 1-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperidin-4-one as prepared in Example 13 (0.15 g, 0.53 mmol) and sodium triacetoxyborohydride (0.112 g, 0.53 mmol). The reaction was stirred at room temperature for 48 hours. The solvent was removed and the residue purified using preparative TLC (10:1 DCM:MeOH) to yield (3R)-3-({1-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl](4-piperidyl)}amino)-1-(4-chlorophenyl)pyrrolidin-2-one.

Workup

  1. customThe solvent was removed
  2. customthe residue purified

Sources & evidence

ORD record
ord-45c4e6ce6e184dcab253ae76f22fd1e5
Source dataset
uspto-grants-2008_11
Patent number
US07452889B2

Reaction notes

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