Benzyl chloroformate → (1-Cyano-2-cyclopropyl-1-methyl-ethyl)-carbamic acid benzyl ester

HRID 1480124

Reaction equation

[NH2:1][C:2]([CH3:9])([CH2:5][CH:6]1[CH2:8][CH2:7]1)[C:3]#[N:4].CCN(C(C)C)C(C)C.[C:19](Cl)(=[O:28])[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1>[CH2:21]([O:20][C:19](=[O:28])[NH:1][C:2]([C:3]#[N:4])([CH3:9])[CH2:5][CH:6]1[CH2:8][CH2:7]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 45 °C

Procedure

To a solution of 2-Amino-3-cyclopropyl-2-methyl-propionitrile (Example 66a, 5.01 g, 30.9 mmol) in dry THF (119 mL) was added DIEA (12.1 mL, 67.9 mmol) and benzyl carbonochloridate (CAN 501-53-1, 5.57 mL, 37.1 mmol). The reaction was stirred at 45° C. for 18 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethylacetate and extracted with an 1.0M aqueous solution of sodium bicarbonate. The organic layer was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography eluting with a gradient of heptane/ethylacetate to yield the title compound (6.2, 60%) as a colorless oil. MS (ESI, m/z): 259.5 (M+H+).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
dissolutionThe residue was dissolved in ethylacetate
extractionextracted with an 1.0M aqueous solution of sodium bicarbonate
dry with materialThe organic layer was dried over sodium sulfate
customevaporated down to dryness
customThe crude material was purified by flash chromatography
washeluting with a gradient of heptane/ethylacetate

Sources & evidence

ORD record: ord-05123ffb9a4543f9a9175e88a87b33c5
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409866B2

Linked notes

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