4-Methylmorpholine → HCID 86761673, compound

HRID 1875330Notes

Reaction equation

HRID 1875330 reaction equation
[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([OH:14])=O)[CH:8]=2)[CH2:3]1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:46]1[CH2:50][CH2:49][C@@H:48]([NH:51][C:52](=[O:58])[O:53][C:54]([CH3:57])([CH3:56])[CH3:55])[CH2:47]1>CN(C=O)C>[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]([N:46]3[CH2:50][CH2:49][C@@H:48]([NH:51][C:52](=[O:58])[O:53][C:54]([CH3:56])([CH3:55])[CH3:57])[CH2:47]3)=[O:14])[CH:8]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57423969HCID 57423969, compound

Product 1

HCID 86761673HCID 86761673, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.1 g (4.8 mmol) 2-methyl-1,2,3,4-tetrahydroisoquinoline-6-carboxylic acid (as hydrochloride) are dissolved in 12 ml DMF, mixed with 2.1 ml (19.3 mmol) NMM and 1.8 g (4.8 mmol) HATU and stirred for five minutes at RT. Then 0.9 g (4.8 mmol) tert. Butyl (R)-pyrrolidin-3-yl-carbamate are added and the mixture is stirred for 16 hours. Then the mixture is poured onto water and extracted with DCM. The organic phase is separated using a phase separation cartridge and evaporated to dryness i. vac. The residue is purified by flash chromatography on silica gel (eluant DCM/MeOH 9:1 to 8:2).

Workup

  1. stirringthe mixture is stirred for 16 hours
  2. additionThen the mixture is poured onto water
  3. extractionextracted with DCM
  4. customThe organic phase is separated
  5. customa phase separation cartridge
  6. customevaporated to dryness i
  7. customThe residue is purified by flash chromatography on silica gel (eluant DCM/MeOH 9:1 to 8:2)

Sources & evidence

ORD record
ord-2f1e97eb315640ac84214f719f63568b
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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