Pyrrolidine → HCID 86702748, compound

HRID 2280078Notes

Reaction equation

HRID 2280078 reaction equation
CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl[C:45]1[CH:54]=[CH:53][CH:52]=[C:51]2[C:46]=1[CH:47]=[C:48]1[CH2:67][C:59]3([CH2:64][O:63][C:62]([CH3:66])([CH3:65])[O:61][CH2:60]3)[CH2:58][C:49]1=[C:50]2[C:55](=[O:57])[CH3:56].[NH:68]1[CH2:72][CH2:71][CH2:70][CH2:69]1>C1COCC1.CCCCCC.CCOC(C)=O>[CH3:66][C:62]1([CH3:65])[O:63][CH2:64][C:59]2([CH2:58][C:49]3=[C:50]([C:55](=[O:57])[CH3:56])[C:51]4[C:46]([CH:47]=[C:48]3[CH2:67]2)=[C:45]([N:68]2[CH2:72][CH2:71][CH2:70][CH2:69]2)[CH:54]=[CH:53][CH:52]=4)[CH2:60][O:61]1

Participants

7

Reactant 4

HCID 31268PyrrolidineHCID 2733832Lithium HexamethyldisilazideHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylHCID 86702742HCID 86702742, compound

Product 1

HCID 86702748HCID 86702748, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Follows general procedure (pag. 13): [RuPhos Palladacyle] (0.0020 g, 0.0028 mmol), LHMDS (0.23 mL of a 1.0 M solution in THF, 0.23 mmol), 5a (0.040 g, 0.12 mmol) in THF (0.3 mL), pyrrolidine (0.014 mL, 0.17 mmol). The title compound was isolated (n-hexane/AcOEt 8:2, 0.016 g, 35% yield) as a yellow solid.

Sources & evidence

ORD record
ord-8aeee4ceff6a44788eb25cbd9b5e836e
Source dataset
uspto-grants-2015_09
Patent number
US09133234B2

Reaction notes

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