Sodium triacetoxyborohydride → HCID 86612286, compound

HRID 2074417Notes

Reaction equation

HRID 2074417 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][C@@H:6]([CH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)[O:7][C@H:8]2[CH2:14][NH:15][CH:16]=[O:17].[Cl:24][C:25]1[CH:38]=[CH:37][C:28]([C:29]([NH:31][CH:32]([CH3:36])[CH2:33][CH:34]=O)=[O:30])=[CH:27][CH:26]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[Cl:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([NH:31][CH:32]([CH3:36])[CH2:33][CH2:34][N:21]2[CH2:20][CH2:19][CH:18]([C@@H:6]3[CH2:5][C:4]4[C:9](=[CH:10][CH:11]=[C:12]([CH3:13])[C:3]=4[O:2][CH3:1])[C@H:8]([CH2:14][NH:15][CH:16]=[O:17])[O:7]3)[CH2:23][CH2:22]2)=[O:30])=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 11695413HCID 11695413, compoundHCID 86612287HCID 86612287, compound

Product 1

HCID 86612286HCID 86612286, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Stir a suspension of N-((1R,3S)-5-methoxy-6-methyl-3-(4-piperidinyl)-1-isochromanylmethyl)formamide (1.0 mmol) with 4-Chloro-N-(1-methyl-3-oxo-propyl)-benzamide (3.0 mmol) and sodium triacetoxyborohydride (3.0 mmol) in dichloromethane (5 mL) at room temperature overnight. Apply the reaction mixture directly to a 5 g SCX column and elute and concentrate the appropriate fractions to obtain the title compound. Use the compound directly for the next step.

Workup

  1. washApply the reaction mixture directly to a 5 g SCX column and elute
  2. concentrationconcentrate the appropriate fractions

Sources & evidence

ORD record
ord-d549cbbbfcfd4cfa816f7753bd9a34cc
Source dataset
uspto-grants-2011_04
Patent number
US07919508B2

Reaction notes

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