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

HRID 855594Notes

Reaction equation

HRID 855594 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-f7c2dcc7c731477bb917e57ba1fe30ab
Source dataset
uspto-grants-2007_08
Patent number
US07262198B2

Reaction notes

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