N,O-Dimethylhydroxylamine → Tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate

HRID 1099306Notes

Reaction equation

HRID 1099306 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[CH3:40][NH:41][O:42][CH3:43]>CN(C=O)C>[CH3:43][O:42][N:41]([CH3:40])[C:14]([CH:10]1[O:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]1)=[O:16]

Participants

6

Reactant 4

HCID 14232N,O-DimethylhydroxylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27559654-((Tert-butoxy)carbonyl)morpholine-2-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 57449675Tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Commercially available 4-(tert-butoxycarbonyl)morpholine-2-carboxylic acid (1.95 g, 8.43 mmol), 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (1.94 g, 10.1 mmol) and 1-hydroxybenztriazole monohydrate (1.25 g, 9.28 mmol) were combined in DMF (10 mL) and stirred at rt for 15 min. before adding N,O-dimethylhydroxylamine (0.987 g, 10.1 mmol), The reaction was stirred at rt overnight. The reaction was then concentrated and partitioned between saturated NaHCO3 and 20% isopropanol in CHCl3. The organic layer was dried (MgSO4) and concentrated. The crude residue was pulled through a layer of silica using CH2Cl2 and the eluting solvent. A colorless oil was isolated (0.7 g, 30%). 1H-NMR (DMSO-d6) δ 4.31-4.18 (bs, 1 H), 3.94-3.78 (m, 2 H), 3.76-3.61 (m, 4 H), 3.48 (dt, J1=11 Hz, J2=2.7 Hz, 1 H), 3.19-2.80 (m, 5 H), 1.39 (s, 9 H).

Workup

  1. stirringThe reaction was stirred at rt overnight
  2. concentrationThe reaction was then concentrated
  3. custompartitioned between saturated NaHCO3 and 20% isopropanol in CHCl3
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated
  6. customA colorless oil was isolated (0.7 g, 30%)

Sources & evidence

ORD record
ord-03a09dcb4e11408bb64c033fcf00b6dd
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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