Triethylamine → (4S)-1-Boc-4-benzyl-L-proline

HRID 1156807Notes

Reaction equation

HRID 1156807 reaction equation
Cl.[CH2:2]([C@@H:9]1[CH2:13][NH:12][C@H:11]([C:14]([OH:16])=[O:15])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:24]([O:28][C:29](ON=C(C1C=CC=CC=1)C#N)=[O:30])([CH3:27])([CH3:26])[CH3:25]>O.O1CCOCC1>[CH3:25][C:24]([CH3:27])([O:28][C:29]([N:12]1[CH2:13][C@@H:9]([CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:10][C@H:11]1[C:14]([OH:16])=[O:15])=[O:30])[CH3:26]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 70070943HCID 70070943, compound

Product 1

HCID 11012191(4S)-1-Boc-4-benzyl-L-proline

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of cis-4-benzyl-L-proline hydrochloride (3 g) and triethylamine (5 g) in water (10 ml) is added a solution of 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (3.5 g) in dioxane (10 ml). The mixture is stirred at ambient temperature for 4 hours. After the addition of water (30 ml), and washing with ether, the mixture is acidified to a pH of 3-4 with 10% citric acid. The oil that separates is extracted into ethyl acetate, washed with brine, and dried (MgSO4). After concentration in vacuo, the residue (3.7 g) solidifies at room temperature, melting point 145°-149° C. dec.

Workup

  1. washwashing with ether
  2. extractionThe oil that separates is extracted into ethyl acetate
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationAfter concentration in vacuo
  6. customsolidifies at room temperature

Sources & evidence

ORD record
ord-d1f21857ffad4218b67a1d693109141d
Source dataset
uspto-grants-1982_06
Patent number
US04337201

Reaction notes

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