N,N,N',N'-Tetramethylethylenediamine → HCID 20664067, compound

HRID 1068201Notes

Reaction equation

HRID 1068201 reaction equation
[CH3:1]N(C)CCN(C)C.[Si:9]([O:16][CH2:17][C@@H:18]1[C@@H:22]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)[CH2:21][N:20]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:19]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].C([Li])(CC)C.CCCCCC>C(OCC)C.C(OCC)(=O)C>[CH3:1][CH:19]1[C@H:18]([CH2:17][O:16][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[C@@H:22]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=2)[CH2:21][N:20]1[C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]

Participants

7

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8058HexaneHCID 20664105HCID 20664105, compoundHCID 178418400CID 53628100

Product 1

HCID 20664067HCID 20664067, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

N,N,N′,N′-Tetramethylethylenediamine (0.268 mL, 2.4 mmol) was added to a solution of 3-(R)-((tert-butyldimethylsilyloxy)methyl)-4-(S)-(3-fluorophenyl)-1-tert-butoxycarbonylpyrrolidine (1.0 g, 2.4 mmol, from Step A) in 5 mL of diethyl ether at −78° C. under nitrogen. sec-Butyllithium (2.2 mL, 1.3M in cyclohexane, 2.8 mmol) was then added dropwise. After 45 min., (MeO)2SO2 (0.298 mL, 4.8 mmol) was added, and the reaction mixture was slowly warmed to room temperature overnight. The reaction was quenched with 5 mL of sat. aq. ammonium chloride, and the mixture was partitioned between diethyl ether and water. The aqueous layer was extracted three times with diethyl ether and the combined organic extracts were dried over Na2SO4. Flash chromatography (95:5 hexane:ethyl acetate) provided 210 mg (21% yield) of the title compound, contaminated with small amounts of the other regioisomer. ESI-MS (M+H): 424.3; HPLC A: 5.33 min.

Workup

  1. customThe reaction was quenched with 5 mL of sat. aq. ammonium chloride
  2. customthe mixture was partitioned between diethyl ether and water
  3. extractionThe aqueous layer was extracted three times with diethyl ether
  4. dry with materialthe combined organic extracts were dried over Na2SO4

Sources & evidence

ORD record
ord-70c0ea9f8b3c4b5a80435297cd1922ba
Source dataset
uspto-grants-2001_06
Patent number
US06248755B1

Reaction notes

Loading…