Morpholine → HCID 69736315, compound

HRID 1374530Notes

Reaction equation

HRID 1374530 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[C:7]([N:14]1[CH2:20][CH2:19][CH2:18][C@H:15]1[CH:16]=O)([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].N1C=CC=CC=1.B>C(Cl)Cl.[Cl-].[Zn+2].[Cl-]>[N:1]1([CH2:16][C@@H:15]2[CH2:18][CH2:19][CH2:20][N:14]2[C:7]([O:9][C:10]([CH3:11])([CH3:13])[CH3:12])=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 2723995Borane;pyridineHCID 2734674tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

Product 1

HCID 69736315HCID 69736315, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

Part A. Morpholine (7.1 g, 7.1 mL, 82 mmol) was added to a stirring solution of N-BOC-(S)-prolinal (3.3 g, 17 mmol) in methylene chloride (83 mL) followed by zinc chloride (0.5 M in THF, 100 mL, 50 mmol). After stirring at ambient temperature for 5 h, borane-pyridine (ca. 8 M, 2 mL, 16 mmol) was added. After stirring at ambient temperature overnight, the reaction was evaporated in vacuo. Methanol was added to the residue and the solids were filtered. Evaporation of the filtrate afforded 13 g of crude product. Purification over silica gel afforded 3.9 g (87%) of 1,1-dimethylethyl (S)-2-(4-morpholinylmethyl)-1-pyrrolidinecarboxylate: 1H-NMR (CDCl3) δ 3.90 (1H, m), 3.69 (4H, m), 3.34 (2H, m), 2.57 (2H, m), 3.40 (2H, m), 2.18 (1H, m), 1.90 (4H, m), 1.74 (1H, m), 1.47 (9H, s).

Workup

  1. stirringAfter stirring at ambient temperature overnight
  2. customthe reaction was evaporated in vacuo
  3. additionMethanol was added to the residue
  4. filtrationthe solids were filtered
  5. customEvaporation of the filtrate
  6. customafforded 13 g of crude product
  7. customPurification over silica gel

Sources & evidence

ORD record
ord-555e3cca573841a9b1084cee38b94f38
Source dataset
uspto-grants-2007_01
Patent number
US07166586B2

Reaction notes

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