Diisopropylamine → HCID 68453297, compound

HRID 2114363Notes

Reaction equation

HRID 2114363 reaction equation
[Li]CCCC.[CH3:6][C:7]([O-:10])([CH3:9])[CH3:8].[K+].C(NC(C)C)(C)C.[C:19]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:24]=[CH:23][C:22]([CH:25]([N:27](C(OC(C)(C)C)=O)[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH3:26])=[CH:21][CH:20]=1.C1C[O:51][CH2:50]C1>Cl>[C:19]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:24]=[CH:23][C:22]([C@@:25]([C:50]([O:10][C:7]([CH3:9])([CH3:8])[CH3:6])=[O:51])([CH3:26])[NH:27][C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])=[CH:21][CH:20]=1

Participants

7

Reactant 5

HCID 7912DiisopropylamineHCID 8028Tetrahydrofuran2×HCID 23665647Potassium tert-butoxideHCID 59809680HCID 59809680, compoundHCID 178418339Butyllithium

Product 1

HCID 68453297HCID 68453297, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

n-BuLi (4.09 ml, 6.5 mmol, 1.6 M in hexane) was added to a suspension of t-BuOK (735 mg, 6.55 mmol) and diisopropyl amine (926 ul, 6.55 mmol) in THF (20 ml) at −78° C. The mixture was stirred at −78° C. for 15 min. before a solution of bis(1,1-dimethylethyl) [1-(4-biphenylyl)ethyl]imidodicarbonate (2.08 g, 5.24 mmol ) in THF (20 ml) was added dropwise and stirring was continued for 30 min at −78° C. The reaction mixture was diluted with HCl (2M, 50 ml) and the product was extracted with ether (3×30 ml). The ether extracts were concentrated and then purified by silica gel chromatography (120 g Redisep column, silica, 40 um, 60 Å, 85 mL/min, A: hexane, B: ethyl acetate, B: 4% for 2 min, 10% for 30 min, detection at 214 nm) which gave 1.15 g (55%) as a clear oil. 1H NMR(CDCl3): delta 7.38-7.63 (m, 9H, arom), 5.95 (1H), 2.01 (3H), 1.41 (S, 18H)

Workup

  1. additionwas added dropwise
  2. extractionthe product was extracted with ether (3×30 ml)
  3. concentrationThe ether extracts were concentrated
  4. custompurified by silica gel chromatography (120 g Redisep column, silica, 40 um, 60 Å, 85 mL/min
  5. waitA: hexane, B: ethyl acetate, B: 4% for 2 min
  6. wait10% for 30 min
  7. customdetection at 214 nm) which gave 1.15 g (55%) as a clear oil

Sources & evidence

ORD record
ord-0f9a48abf89f4debaab45c018a4a949d
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

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