Acetic Acid → HCID 66750644, compound

HRID 643927Notes

Reaction equation

HRID 643927 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH2:13][CH2:14][CH2:15]2)=[CH:11][C:10]=1[NH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]([OH:22])=[O:21].[C:23](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC#N>[CH3:23][O:21][C:20](=[O:22])[CH2:19][NH:18][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:15][CH2:14][CH2:13]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 13821912HCID 13821912, compound

Product 1

HCID 66750644HCID 66750644, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 6-benzyloxyindan-5-ylamine (2.00 g, 8.37 mmol) in MeCN (50 mL) is added AcOH (25 mL) followed by ethyl gloxylate (50% in toluene, 2.49 mL, 12.6 mmol). This is stirred for 2 h, then cooled to 0° C. A slurry of sodium triacetoxyborohydride (3.55 g, 16.7 mmol) is added and this is stirred for 10 min, at which time LCMS reveals complete consumption of the starting material. The reaction is diluted with saturated NaHCO3 and DCM, and the organic layer is separated, washed with brine, dried over MgSO4 and concentrated in vacuo to afford (6-benzyloxyindan-5-ylamino)-acetic acid methyl ester as a brown gummy solid.

Workup

  1. stirringthis is stirred for 10 min, at which time LCMS
  2. customconsumption of the starting material
  3. additionThe reaction is diluted with saturated NaHCO3 and DCM
  4. customthe organic layer is separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1ec99a6d7bc145ee98b5872cbc7106fb
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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