Morpholine → HCID 69736315, compound

HRID 1267845Notes

Reaction equation

HRID 1267845 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 tn 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) δ3.90 (1 H, m), 3.69 (4 H, m), 3.34 (2 H, m), 2.57 (2 H, m), 3.40 (2 H, m), 2.18 (1 H, m), 1.90 (4 H, m), 1.74 (1 H, m), 1.47 (9 H, s).

Workup

  1. stirringAfter stirring at ambient temperature overnight
  2. customthe reaction was evaporated tn 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-ea2eeeabfc9b45c7a8a17965dadff6aa
Source dataset
uspto-grants-2003_04
Patent number
US06555542B1

Reaction notes

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