4-Benzhydryloxypiperidine → HCID 86680286, compound

HRID 2202581Notes

Reaction equation

HRID 2202581 reaction equation
[CH:1]([O:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21]([O:25][C:26]([N:28]1[C:32]([CH:33]=O)=[CH:31][CH:30]=[C:29]1[C:35]([O:37][CH3:38])=[O:36])=[O:27])([CH3:24])([CH3:23])[CH3:22].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:38][O:37][C:35]([C:29]1[N:28]([C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[C:32]([CH2:33][N:18]2[CH2:19][CH2:20][CH:15]([O:14][CH:1]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:16][CH2:17]2)=[CH:31][CH:30]=1)=[O:36]

Participants

5

Reactant 3

HCID 30175844-BenzhydryloxypiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 86680287HCID 86680287, compound

Product 1

HCID 86680286HCID 86680286, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a 100-mL three-neck flask, 1.1 g (4.0 mmol) of 4-benzhydryloxypiperidine synthesized in Production Example 1, 1.0 g (4.0 mmol) of methyl N-tert-butoxycarbonyl-5-formylpyrrole-2-carboxylate, and 20 mL of dichloromethane were fed under an argon atmosphere, and the internal temperature was cooled to 0° C. Thereinto, 1.3 g (6.1 mmol, 1.5 eq.) of sodium triacetoxyborohydride was added at an internal temperature of not higher than −5° C., and the mixture was stirred for 5 minutes at the same temperature. Then, the mixture was heated to a room temperature and stirred overnight.

Workup

  1. temperatureThen, the mixture was heated to a room temperature
  2. stirringstirred overnight

Sources & evidence

ORD record
ord-5613559267fa4be1818c30749056768c
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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