Acetic Acid → HCID 59383059, compound

HRID 2355453Notes

Reaction equation

HRID 2355453 reaction equation
[CH:1]1([C@H:6]([OH:21])[C@H:7]([N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])[CH:8]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(=O)C.[CH3:26][NH2:27].C(Cl)Cl>C1COCC1>[CH:1]1([C@H:6]([OH:21])[C@H:7]([N:10]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]2=[O:20])[CH2:8][NH:27][CH3:26])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 6344DichloromethaneHCID 59383068HCID 59383068, compound

Product 1

HCID 59383059HCID 59383059, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2S,3S)-3-cyclopentyl-3-hydroxy-2-(1,3-dioxoisoindolin-2-yl)propanal (1.339 g, 4.7 mmol) in dry THF (20 mL) was cooled to 0° C. Acetic acid (2.5 mL, 44 mmol), methylamine (33% in EtOH, 2.5 mL, 20 mmol), and NaHB(OAc) 3 (4.4937 g, 21.3 mmol) were added sequentially in single portions. The ice bath was removed and the mixture was stirred for 2 h at rt. The solvent was stripped and the crude 2-((1S,2R)-1-cyclopentyl-1-hydroxy-3-(methylamino)propan-2-yl)isoindoline-1,3-dione was used directly in the next step. LC-MS (3 min) tR=1.07, m/z=303 (M+1).

Workup

  1. customThe ice bath was removed
  2. customLC-MS (3 min) tR=1.07, m/z=303 (M+1)

Sources & evidence

ORD record
ord-daaf73f3a80c487e8d708fbc55503914
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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