Acetaldehyde → HCID 68292763, compound

HRID 1841995Notes

Reaction equation

HRID 1841995 reaction equation
[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][NH:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C@@H:19]3[O:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[O:21][CH2:20]3)=[CH:15][CH:14]=2)=[CH:6][CH:5]=1.[CH:30](=O)[CH3:31].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:29])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][N:11]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C@@H:19]3[O:24][C:23]4[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=4[O:21][CH2:20]3)=[CH:15][CH:14]=2)[CH2:30][CH3:31])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68292864HCID 68292864, compound

Product 1

HCID 68292763HCID 68292763, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-{[(S)-4-(2,3-dihydro-benzo[1,4]dioxin-2-yl)-benzylamino]-methyl}-benzoic acid methyl ester (prepared according to General Method E) (130 mg, 0.33 mmol), acetaldehyde (0.03 mL, 0.50 mmol), and sodium cyanoborohydride (42 mg, 0.67 mmol) in MeOH (15 mL) is treated with 2 drops of acetic acid. The mixture is stirred at room temperature for 16 h, and concentrated. The residue is purified by flash chromatography eluting with a gradient of 0-10% MeOH in DCM to give 4-({[(S)-4-(2,3-dihydro-benzo[1,4]dioxin-2-yl)-benzyl]-ethyl-amino}-methyl)-benzoic acid methyl ester.

Workup

  1. concentrationconcentrated
  2. customThe residue is purified by flash chromatography
  3. washeluting with a gradient of 0-10% MeOH in DCM

Sources & evidence

ORD record
ord-f541a2561b5f438493c1730fb4b7d6dc
Source dataset
uspto-grants-2015_02
Patent number
US08946203B2

Reaction notes

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