Acetic Acid → rac-[(3R,4S)-3-(3,4-Dichloro-phenyl)-4-isopropylamino-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone

HRID 527475Notes

Reaction equation

HRID 527475 reaction equation
[NH2:1][CH:2]1[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=2)[CH2:5][N:4]([C:15]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([C:25]3([CH3:28])[CH2:27][CH2:26]3)=[O:24])[CH2:19][CH2:18]2)=[O:16])[CH2:3]1.[CH3:29][C:30]([CH3:32])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[Cl:14][C:9]1[CH:8]=[C:7]([C@H:6]2[C@H:2]([NH:1][CH:30]([CH3:32])[CH3:29])[CH2:3][N:4]([C:15]([CH:17]3[CH2:22][CH2:21][N:20]([C:23]([C:25]4([CH3:28])[CH2:27][CH2:26]4)=[O:24])[CH2:19][CH2:18]3)=[O:16])[CH2:5]2)[CH:12]=[CH:11][C:10]=1[Cl:13]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 67238593rac-(3S,4R)-[3-Amino-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone

Product 1

HCID 67239261rac-[(3R,4S)-3-(3,4-Dichloro-phenyl)-4-isopropylamino-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanoneYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of rac-(3S,4R)-[3-Amino-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone (120 mg, 0.28 mmol) in dichloromethane (1 mL) were added acetone (21 uL, 0.28 mmol) and sodiumtriacetoxy-borohydride (72 mg, 0.34 mmol) and acetic acid (16 uL, 0.28 mmol) and the reaction mixture was stirred at ambient temperature for 3 h. It was diluted with dichloromethane and washed with aqueous sodiumhydrogenecarbonate (1M). The organic layer was dried over sodium sulfate and concentrated affording the title compound (95 mg, 72%) as a light yellow foam. MS m/e: 466.3 [M]+.

Workup

  1. washwashed with aqueous sodiumhydrogenecarbonate (1M)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b1f5d3f418794183afe571eaf96ebb02
Source dataset
uspto-grants-2016_05
Patent number
US09346786B2

Reaction notes

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