Succinic anhydride → HCID 86660752, compound

HRID 1404841Notes

Reaction equation

HRID 1404841 reaction equation
[CH3:1][N:2]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[O:3][CH2:4][CH:5]([OH:7])[CH3:6].[C:15]1(=[O:21])[O:20][C:18](=[O:19])[CH2:17][CH2:16]1.[Cl-].[NH4+]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:14][C:11]([CH3:13])([O:10][C:8](=[O:9])[N:2]([CH3:1])[O:3][CH2:4][CH:5]([CH3:6])[O:7][C:15](=[O:21])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])[CH3:12]

Participants

6

Reactant 3

HCID 7922Succinic anhydrideHCID 25517Ammonium ChlorideHCID 86660753HCID 86660753, compound

Product 1

HCID 86660752HCID 86660752, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-methyl-N-boc-(2-hydroxypropyl)hydroxylamine (227 mg, 1.11 mmol) in dichloromethane (4 mL) were added DMAP (41 mg, 0.333 mmol) and succinic anhydride (167 mg, 1.67 mmol). The resulting mixture was stirred for 20 h at room temperature. The reaction mixture was poured into a saturated solution of ammonium chloride (15 mL) and extracted with DCM (3×40 mL). The combined organic layer was washed with water and dried over sodium sulfate. The solvent was removed in vacuo and the crude product was purified by silica flash column chromatography using 40% EtOAc/hexane as eluent to give the product as a white solid (227 mg, 0.744 mmol, 67%). 1H NMR (CDCl3, 400 MHz): δ (ppm) 1.14 (d, 3H, J=6.4 Hz), 1.45 (s, 9H), 2.51-2.57 (m, 4H), 2.91 (s, 3H), 3.77-3.79 (m, 2H), 5.04-5.11 (m, 1H).

Workup

  1. extractionextracted with DCM (3×40 mL)
  2. washThe combined organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed in vacuo
  5. customthe crude product was purified by silica flash column chromatography

Sources & evidence

ORD record
ord-36218d1ae48d422d90c6c193147ca21b
Source dataset
uspto-grants-2014_12
Patent number
US08916169B2

Reaction notes

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