Dicyclohexylcarbodiimide → (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate

HRID 1619502Notes

Reaction equation

HRID 1619502 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:19]12[CH2:26][CH2:25][CH:22]([CH2:23][CH2:24]1)[C@@H:21](O)[CH2:20]2.C1C=CC2N(O)N=NC=2C=1.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([O:12][C@@H:21]1[CH:22]2[CH2:25][CH2:26][N:19]([CH2:24][CH2:23]2)[CH2:20]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 914043-Quinuclidinol, (-)-HCID 5718052-(((Tert-butoxy)carbonyl)amino)-2-phenylacetic acid

Product 1

HCID 67425060(R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetateYield 58.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(tert-butoxycarbonylamino)-2-phenylacetic acid (I3) (2.00 g, 7.96 mmol), (R)-quinuclidin-3-ol (1.21 g, 9.55 mmol), HOBt (1.46 g, 9.55 mmol), and DCC (1.97 g, 9.55 mmol) in dry THF (70 ml) was stirred at RT overnight. Then THF was evaporated and the crude was taken up with DCM and washed twice with 2M K2CO3 and brine. The organic phase was dried over Na2SO4, filtered, and evaporated to dryness. The crude was purified by flash chromatography (DCM/MeOH=95/5) to get (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate (1.68 g; 58.5% yield).

Workup

  1. customThen THF was evaporated
  2. washwashed twice with 2M K2CO3 and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe crude was purified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record
ord-42f17607660c4ab5b97b8428b9684339
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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