Morpholine → Benzyl (3S)-3-(4-morpholinylcarbonyl)-3,4-dihydro-2(1H)-isoquinoline carboxylate

HRID 2272870Notes

Reaction equation

HRID 2272870 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C@H:20]([C:21]([OH:23])=O)[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(N(CC)CC)C.C(N=C=NCCCN(C)C)C.OC1C2N=NNC=2C=CC=1.[Cl-].[NH4+]>ClCCl>[N:24]1([C:21]([C@@H:20]2[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][N:11]2[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])=[O:23])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1

Participants

8

Reactant 6

HCID 8083MorpholineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 688307(3S)-2-Carbobenzoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic AcidHCID 178418300HCID 178418300, compound

Product 1

HCID 1118330Benzyl (3S)-3-(4-morpholinylcarbonyl)-3,4-dihydro-2(1H)-isoquinoline carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5 g of (3S)-2-[(benzyloxy)carbonyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid (16 mmol) in 160 mL of dichloromethane there are added 1.5 mL of morpholine (17.6 mmol) and then 9 mL of N,N,N-triethylamine (64 mmol), 3.3 g of 1-ethyl-3-(3′-dimethylaminopropyl)-carbodiimide (EDC) (19.2 mmol) and 2.6 g of hydroxybenzotriazole (HOBT) (19.2 mmol). The reaction mixture is stirred at ambient temperature overnight and is then poured onto a solution of ammonium chloride and extracted with ethyl acetate. The organic phase is subsequently dried over magnesium sulphate and then filtered and evaporated to dryness. The crude product so obtained is then purified by chromatography over silica gel (dichloromethane/methanol gradient). The product is obtained in the form of a foam.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase is subsequently dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-361da210d38a4adaa92e842faa1f4378
Source dataset
uspto-grants-2015_09
Patent number
US09120791B2

Reaction notes

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