Isopropenyl chloroformate → Prop-1-en-2-yl (1-methoxycyclopentanecarbonyl)carbamate

HRID 626536Notes

Reaction equation

HRID 626536 reaction equation
[CH3:1][O:2][C:3]1([C:8]([NH2:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl[C:22]([O:24][C:25]([CH3:27])=[CH2:26])=[O:23]>C1COCC1>[CH3:1][O:2][C:3]1([C:8]([NH:10][C:22](=[O:23])[O:24][C:25]([CH3:27])=[CH2:26])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 93846Isopropenyl chloroformateHCID 2733832Lithium HexamethyldisilazideHCID 675281901-Methoxycyclopentanecarboxamide

Product 1

HCID 90445234Prop-1-en-2-yl (1-methoxycyclopentanecarbonyl)carbamateYield 105%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A −78° C. solution of 1-methoxycyclopentanecarboxamide (0.9 g, 6.29 mmol) in THF (40 mL), under Ar, was treated with LiHMDS (1M in THF, 8.17 mL, 8.17 mmol), stirred for 0.5 h, treated with a solution of isopropenyl chloroformate (0.824 mL, 7.54 mmol) in THF (5 mL), stirred at −78° C. for 15 min, warmed to RT and stirred for 1 h. The mixture was treated with satd. NH4Cl, the layers separated and the aqueous layer extracted with EtOAc (1×). The combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford crude prop-1-en-2-yl (1-methoxycyclopentanecarbonyl)carbamate (1.5 g, 105%) which was used without further purification. MS (ESI) m/z: 228.1 (M+H+).

Workup

  1. stirringstirred at −78° C. for 15 min
  2. stirringstirred for 1 h
  3. additionThe mixture was treated with satd
  4. customNH4Cl, the layers separated
  5. extractionthe aqueous layer extracted with EtOAc (1×)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-e2c300e904ed4263b2758a007b6d61b5
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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