Cyclopropylamine → 9H-fluoren-9-ylmethyl 2-[(cyclopropylamino)carbonyl]morpholine-4-carboxylate

HRID 1435500Notes

Reaction equation

HRID 1435500 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:25]1([NH2:28])[CH2:27][CH2:26]1.[CH:29]1[C:41]2[CH:40]([CH2:42][O:43][C:44]([N:46]3[CH2:51][CH2:50][O:49][CH:48]([C:52](O)=[O:53])[CH2:47]3)=[O:45])[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[C:33]=2[CH:32]=[CH:31][CH:30]=1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH:25]1([NH:28][C:52]([CH:48]2[O:49][CH2:50][CH2:51][N:46]([C:44]([O:43][CH2:42][CH:40]3[C:39]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[C:33]4[C:41]3=[CH:29][CH:30]=[CH:31][CH:32]=4)=[O:45])[CH2:47]2)=[O:53])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 27561284-{[(9H-fluoren-9-yl)methoxy]carbonyl}morpholine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 579373209H-fluoren-9-ylmethyl 2-[(cyclopropylamino)carbonyl]morpholine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (1.17 g, 3.0 mmol) and cyclopropylamine (0.17 g, 3.0 mmol) were added to a solution of 4-[(9H-fluoren-9-ylmethoxy)carbonyl]morpholine-2-carboxylic acid (1.0 g, 2.9 mmol) and DIPEA (0.56 mL, 3.2 mmol) in DMF (50 mL). The reaction mixture was stirred for 2 hrs. at ambient temperature and the solvent was concentrated. The product was recovered in EtOAc and washed with water, saturated NaHCO3 solution, water and brine. The organic layer was dried over anhydrous MgSO4 and the solvent was concentrated to provide the title compound that was used for the next step without further purification. MS (ESI) (M+H)+=393.0.

Workup

  1. concentrationat ambient temperature and the solvent was concentrated
  2. customThe product was recovered in EtOAc
  3. washwashed with water, saturated NaHCO3 solution, water and brine
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. concentrationthe solvent was concentrated

Sources & evidence

ORD record
ord-188770e5ffba4498836c524f6fb63420
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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