Acetaldehyde → HCID 68292763, compound

HRID 2276923Notes

Reaction equation

HRID 2276923 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-ed810b7e404542eabccf2c210259ea26
Source dataset
uspto-grants-2015_09
Patent number
US09133146B2

Reaction notes

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